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Tetrahedron Letters

Volumn 36, Issue 37, 1995, Pages 6595-6598

A protection scheme for the preparation of acid chlorides of serine and threonine

(2) Xi, Ning a Ciufolini, Marco A a

a RICE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85012099807 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/00404-0399(50)1348-L Document Type: Article

Times cited : (32)

References (23)

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2
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6
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7
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- may resolve at least some of the problems we encountered, but we have not explored the application of these newer methods to our system.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 4367
- Carpino, L.A.¹

8
- 85024627056
- Cf. Rebert, N.W.; Dissertation, Utah State University, 1987.

9
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- The Total Synthesis of Antrimycin Dv; II:1Synthesis of Tetrahydropyridazinecarboxylic Acid and Its Incorporation into Peptides
- (1993) Synthesis , pp. 809
- Schmidt, U.¹ Riedl, B.²

10
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- For an example requiring activation of the acid chloride by AgCN in a system resembling ours see
- (1994) Tetrahedron Lett. , vol.35 , pp. 7685
- Hale, K.J.¹ Delisser, V.M.² Yeh, L.K.³ Peak, S.A.⁴ Manaviazar, S.⁵ Bhatia, G.S.⁶

11
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- These investigators describe problems very similar to the ones we observed.

12
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- John Wiley & Sons, New York, NY, ch. 5. See especially pp. 132-133 and references cited therein.
- (1987) Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids
- Coppola, G.M.¹ Schuster, H.F.²

13
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- and references cited therein.
- (1986) J. Org. Chem. , vol.51 , pp. 3732
- Carpino, L.A.¹ Cohen, B.J.² Stephens, K.E.³ Sadat-Aalaee, S.Y.⁴ Tien, J.H.⁵ Langridge, D.C.⁶

14
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- Rules for ring closure
- In Baldwin’s parlance, β-elimination would be a retrograde 5-endo-trig process
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15
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- 4th. ed., John Wiley & Sons, New York, NY, see also
- (1992) Advanced Organic Chemistry , pp. 212
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16
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- Selective Cleavage of Serine Peptides
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17
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- CAUTION: extremely hazardous gas. This reaction must be carried out in an efficient hood, with suitable provision for trapping / venting excess reagent that escapes from the reaction vessel.

18
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- 8 116–117° C).

19
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20
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21
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22
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- Because of extremely unfavorable solubility properties, the rotation of 17 could not be measured.

23
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- Compound 17 is poorly soluble in MeOH. Fortunately, a suspension of 17 in MeOH was fully satisfactory for the Kunieda reaction, completion of which was visually signaled by the mixture becoming homogeneous.

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