메뉴 건너뛰기




Volumn 24, Issue 4-6, 2005, Pages 441-462

2-(Dimethyl (2-naphthylmethyl)silyl) ethoxy carbonate (NSEC) as a new mode of hydroxyl group protection

Author keywords

Carbohydrates; Carbonate; Deprotection; Glycosylation; Oligosaccharides; Silyl protecting group

Indexed keywords


EID: 27844444189     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1081/CAR-200067008     Document Type: Article
Times cited : (6)

References (22)
  • 2
    • 0029841253 scopus 로고    scopus 로고
    • Selective deprotection of silyl ethers
    • Nelson, T.D.; Crouch, R.D. Selective deprotection of silyl ethers. Synthesis 1996, 1031-1069.
    • (1996) Synthesis , pp. 1031-1069
    • Nelson, T.D.1    Crouch, R.D.2
  • 3
    • 0032545045 scopus 로고    scopus 로고
    • Novel RNA synthesis method using 5′-O-Silyl-2′-O-orthoester protecting groups
    • Scaringe, S.A.; Wincott, F.E.; Caruthers, M.H. Novel RNA synthesis method using 5′-O-Silyl-2′-O-orthoester protecting groups. J. Am. Chem. Soc. 1998, 120, 11820-11821.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 11820-11821
    • Scaringe, S.A.1    Wincott, F.E.2    Caruthers, M.H.3
  • 4
    • 0034038967 scopus 로고    scopus 로고
    • Recent progress in polymer-supported synthesis of oligosaccharides and carbohydrate libraries
    • Haase, W.C.; Seeberger, P.H. Recent progress in polymer-supported synthesis of oligosaccharides and carbohydrate libraries. Curr. Org. Chem. 2000, 4, 481-511.
    • (2000) Curr. Org. Chem. , vol.4 , pp. 481-511
    • Haase, W.C.1    Seeberger, P.H.2
  • 5
    • 1042276934 scopus 로고    scopus 로고
    • Automated Solid-phase synthesis of protected tumor-associated antigen and blood group determinant oligosaccharides
    • Love, K.R.; Seeberger, P.H. Automated Solid-phase synthesis of protected tumor-associated antigen and blood group determinant oligosaccharides. Angew. Chem. Int. Ed. 2004, 43, 602-605.
    • (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 602-605
    • Love, K.R.1    Seeberger, P.H.2
  • 6
    • 0037011298 scopus 로고    scopus 로고
    • Efficient solid-phase synthesis of a complex, branched N-glycan hexasaccharide: Use of a novel linker and temporary protecting-group pattern
    • A similar technique has been used for the solid-phase synthesis of a complex-type N-glycan hexasaccharide: Wu, X.; Grathwohl, M.; Schmidt, R.R. Efficient solid-phase synthesis of a complex, branched N-glycan hexasaccharide: use of a novel linker and temporary protecting-group pattern. Angew. Chem. Int. Ed. 2002, 41, 4489-4493.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 4489-4493
    • Wu, X.1    Grathwohl, M.2    Schmidt, R.R.3
  • 8
    • 0007524897 scopus 로고
    • 2-(Trimethylsilyl) ethyl chloroformate: A convenient reagent for protection of the hydroxyl function
    • Gioeli, C.; Balgobin, N.; Josephson, S.; Chattopadhyaya, J.B. 2-(Trimethylsilyl) ethyl chloroformate: a convenient reagent for protection of the hydroxyl function. Tetrahedron Lett. 1981, 22, 969-972.
    • (1981) Tetrahedron Lett. , vol.22 , pp. 969-972
    • Gioeli, C.1    Balgobin, N.2    Josephson, S.3    Chattopadhyaya, J.B.4
  • 9
    • 0003020992 scopus 로고
    • Synthesis and evaluation of novel activated mixed carbonate reagents for the introduction of the 2-(trimethylsilyl)ethoxycarbonyl (Teoc) protecting group
    • Shute, R.E.; Rich, D.H. Synthesis and evaluation of novel activated mixed carbonate reagents for the introduction of the 2-(trimethylsilyl)ethoxycarbonyl (Teoc) protecting group. Synthesis 1987, 346-349.
    • (1987) Synthesis , pp. 346-349
    • Shute, R.E.1    Rich, D.H.2
  • 10
    • 3242801996 scopus 로고    scopus 로고
    • Lewis acid deprotection of silyl-protected oligonucleotides and base-sensitive oligonucleotide analogs
    • Ferreira, F.; Vasseur, J.-J.; Morvan, F. Lewis acid deprotection of silyl-protected oligonucleotides and base-sensitive oligonucleotide analogs. Tetrahedron Lett. 2004, 45, 6287-6290.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 6287-6290
    • Ferreira, F.1    Vasseur, J.-J.2    Morvan, F.3
  • 11
    • 27844460155 scopus 로고    scopus 로고
    • Synthesis of N-(trimethylsilylethoxycarbonyl)deoxycytidine and deoxyadenosine derivatives as key intermediates for the DNA synthesis using fluoride ion-promoted deprotection strategy
    • Sekine, M.; Tobe, M.; Nagayama, T.; Wada, T. Synthesis of N-(trimethylsilylethoxycarbonyl)deoxycytidine and deoxyadenosine derivatives as key intermediates for the DNA synthesis using fluoride ion-promoted deprotection strategy. Lett. Org. Chem. 2004, 1, 179-182.
    • (2004) Lett. Org. Chem. , vol.1 , pp. 179-182
    • Sekine, M.1    Tobe, M.2    Nagayama, T.3    Wada, T.4
  • 14
    • 37049109112 scopus 로고
    • Acid-catalyzed benzylation and allylation by alkyl trichloroacetimidates
    • Wessel, H.P.; Iversen, T.; Bundle, D.R. Acid-catalyzed benzylation and allylation by alkyl trichloroacetimidates. J. Chem. Soc., Perkin Trans. 1 1985, 1, 2247-2250.
    • (1985) J. Chem. Soc., Perkin Trans. 1 , vol.1 , pp. 2247-2250
    • Wessel, H.P.1    Iversen, T.2    Bundle, D.R.3
  • 15
    • 0030662091 scopus 로고    scopus 로고
    • Coupling of glycal derived thioethyl glycosyl donors with glycal acceptors. An important advance in the scope of the glycal assembly
    • Seeberger, P.H.; Eckhardt, M.; Gutteridge, C.E.; Danishefsky, S.J. Coupling of glycal derived thioethyl glycosyl donors with glycal acceptors. An important advance in the scope of the glycal assembly. J. Am. Chem. Soc. 1997, 119, 10064-10072.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10064-10072
    • Seeberger, P.H.1    Eckhardt, M.2    Gutteridge, C.E.3    Danishefsky, S.J.4
  • 16
    • 0033614879 scopus 로고    scopus 로고
    • Synthesis and use of glycosyl phosphates as glycosyl donors
    • Plante, O.J.; Andrade, R.B.; Seeberger, P.H. Synthesis and use of glycosyl phosphates as glycosyl donors. Org. Lett. 2001, 1, 211-214.
    • (2001) Org. Lett. , vol.1 , pp. 211-214
    • Plante, O.J.1    Andrade, R.B.2    Seeberger, P.H.3
  • 17
    • 0043190496 scopus 로고
    • Vinylmetalloids. 2. High regioselectivity of dialkylboranes in hydroboration of vinyltrimethylsilane
    • Soderquist, J.A.; Hassner, A. Vinylmetalloids. 2. High regioselectivity of dialkylboranes in hydroboration of vinyltrimethylsilane. J. Organomet. Chem. 1978, 156, C12-C16.
    • (1978) J. Organomet. Chem. , vol.156
    • Soderquist, J.A.1    Hassner, A.2
  • 18
    • 84971061986 scopus 로고
    • Studies on unsaturated sugars with particular reference to the synthesis of 6-deoxy-6-fluoro derivatives
    • Blackburne, I.D.; Fredericks, P.M.; Guthrie, R.D. Studies on unsaturated sugars with particular reference to the synthesis of 6-deoxy-6-fluoro derivatives. Australian J. Chem. 1976, 29, 381-391.
    • (1976) Australian J. Chem. , vol.29 , pp. 381-391
    • Blackburne, I.D.1    Fredericks, P.M.2    Guthrie, R.D.3
  • 19
    • 0035122650 scopus 로고    scopus 로고
    • Para-chlorophenyl carbonate as a versatile hydroxyl protecting group
    • Love, K.R.; Seeberger, P.H. Para-chlorophenyl carbonate as a versatile hydroxyl protecting group. Synthesis 2001, 317-322.
    • (2001) Synthesis , pp. 317-322
    • Love, K.R.1    Seeberger, P.H.2
  • 20
    • 0035977215 scopus 로고    scopus 로고
    • Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks
    • Love, K.R.; Andrade, R.B.; Seeberger, P.H. Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks. J. Org. Chem. 2001, 66, 8165-8176.
    • (2001) J. Org. Chem. , vol.66 , pp. 8165-8176
    • Love, K.R.1    Andrade, R.B.2    Seeberger, P.H.3
  • 21
    • 0035802334 scopus 로고    scopus 로고
    • Oligosaccharide synthesis with glycosyl phosphate and dithiophosphate triesters as glycosylating agents
    • Plante, O.J.; Palmacci, E.R.; Andrade, R.B.; Seeberger, P.H. Oligosaccharide synthesis with glycosyl phosphate and dithiophosphate triesters as glycosylating agents. J. Am. Chem. Soc. 2001, 123, 9545-9554.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9545-9554
    • Plante, O.J.1    Palmacci, E.R.2    Andrade, R.B.3    Seeberger, P.H.4
  • 22
    • 0034718086 scopus 로고    scopus 로고
    • Halobenzyl ethers as protecting groups for organic synthesis
    • Plante, O.J.; Buchwald, S.L.; Seeberger, P.H. Halobenzyl ethers as protecting groups for organic synthesis. J. Am. Chem. Soc. 2000, 122, 7148-7149.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7148-7149
    • Plante, O.J.1    Buchwald, S.L.2    Seeberger, P.H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.