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Tetrahedron Letters

Volumn 21, Issue 35, 1980, Pages 3343-3346

β-(Trimethylsilyl)ethoxymethyl chloride. A new reagent for the protection of the hydroxyl group

(2) Lipshutz, Bruce H a Pegram, Joseph J a

a UNIVERSITY OF CALIFORNIA (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001515913 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)78684-9 Document Type: Article

Times cited : (207)

References (24)

1
- 0003851633
- Plenum Press, London
- (1973) Protective Groups in Organic Chemistry
- McOmie¹

2
- 29644432244
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 6190
- Corey¹ Venkateswarlu²

3
- 0015244827
- (1971) J. Am. Chem. Soc. , vol.93 , pp. 7319
- Corey¹ Varma²

4
- 0002375739
- For a recent review, see
- (1978) Chem. Soc. Rev. , vol.7 , pp. 15
- Colvin¹

5
- 84914346380
- For convenience, we use the expression 'SEM-Cl', from β-(trimethylSilyl)EthoxyMethyl chloride.

6
- 49549134009
- (1976) Tetrahedron Letters , pp. 809
- Corey¹ Gras² Ulrich³

7
- 0043190496
- from vinyltrimethylsilane, via hydroboration
- (1978) J. Organomet. Chem. , vol.156 , pp. C12
- Sonderquist¹ Hassner²

8
- 0000234050
- from vinyltrimethylsilane, via oxymercuration
- (1978) J. Organomet. Chem. , vol.159 , pp. 237
- Sonderquist¹ Thompson²

9
- 33947336160
- from ethyl bromoacetate, via a Reformatsky/LAH sequence
- (1967) J. Org. Chem. , vol.32 , pp. 3535
- Fessenden¹ Fessenden²

10
- 84985095006
- (1977) Helv. Chim. Acta , vol.60 , pp. 3039
- Gerlach¹

11
- 84914346379
- Use of paraformaldehyde is essential to the success of the reaction. Substitution of s-trioxane leads to impure SEM-Cl in ca. 15% yield.

12
- 84914346378
- NMR analysis revealed only the expected absorptions.

13
- 84914346377
- The reagent can best be stored in a refrigerator in a well-sealed container under an inert atmosphere.

14
- 84914346376
- All new compounds gave satisfactory ir, nmr, and mass spectral data (both low and high resolution).

15
- 84914346375
- Use of this mixed ketal derived from the dimethyl ketal of p-methoxyacetophenone will be reported shortly; M. Morey and B.H. Lipshutz, unpublished data.

16
- 37049113239
- The ?-(trimethylsilyl)ethoxycarbonyl amino-protecting group
- For a similar effect involving the use of fluoride ion, see
- (1978) Journal of the Chemical Society, Chemical Communications , pp. 358
- Carpino¹ Tsao²

17
- 84985080215
- (1977) Helv. Chim. Acta , vol.60 , pp. 2711
- Sieber¹

18
- 84855548220
- Hydroxyl Protection. III. Synthesis and Cleavage of 2-(Phenylseleno)Ethyl Ethers
- Other representative (carboxyl or hydroxyl) protecting groups wherein sequential elimination processes take place in an analogous fashion to that described herein include
- (1975) Synthetic Communications , vol.5 , pp. 367
- Ho¹ Hall²

19
- 84949161376
- Carboxyl Protection Facile Cleavage of 2-Haloethyl Esters with Sodium Hydrogen Selenide
- (1978) Synthetic Communications , vol.8 , pp. 301
- Ho¹

20
- 0000749498
- Trimethylstannyl Group as Pivot in Cleavage of 2-Bromoethyl Esters
- (1978) Synthetic Communications , vol.8 , pp. 359
- Ho¹

21
- 0007762233
- New Alcohol Protecting Groups. β,β,β-Trichloroethoxymethyl Ethers
- (1979) Synthetic Communications , vol.9 , pp. 57
- Jacobson¹ Clader²

22
- 84914346374
- From Eastman Organic Chemicals, Rochester, New York.

23
- 84984075475
- Synthetic applications of 2-chlorotetrahydrofuran: Protection of alcohols as tetrahydro-2-furanyl (THF) ethers
- The THF protecting group can be removed much more easily than the corresponding THP ether; for a review, see
- (1979) Recueil des Travaux Chimiques des Pays-Bas , vol.98 , pp. 371
- Kruse¹ Jonkers² Dert³ van der Gen⁴

24
- 84914346373
- SEM-Cl will soon be available from the Aldrich Chemical Company, Milwaukee, Wisconsin.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.