BOC-CIS-3-HYDROXY-D-PROLINE

Base Information

• Chemical Name: BOC-CIS-3-HYDROXY-D-PROLINE
• CAS No.: 118492-87-8
• Molecular Formula: C₁₀H₁₇NO₅
• Molecular Weight: 231.249
• Mol file: 118492-87-8.mol

Synonyms:1,2-Pyrrolidinedicarboxylicacid, 3-hydroxy-, 1-(1,1-dimethylethyl) ester, (2R-cis)-

Chemical Property of BOC-CIS-3-HYDROXY-D-PROLINE

Chemical Property:

• Melting Point: 101-103 °C
• Boiling Point: 390.9±42.0 °C(Predicted)
• PKA: 3.69±0.40(Predicted)
• PSA: 87.07000
• Density: 1.312
• LogP: 0.37920

Purity/Quality:

98.5% ^*data from raw suppliers

Boc-cis-3-hydroxy-D-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Boc-cis-3-hydroxy-D-proline is a useful research chemical.

Technology Process of BOC-CIS-3-HYDROXY-D-PROLINE

There total 12 articles about BOC-CIS-3-HYDROXY-D-PROLINE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

cis-3-hydroxy-DL-proline (4298-05-9) + tert-butyl chloroformate (24608-52-4) → cis-N-(tert-butoxycarbonyl)-3-hydroxy-DL-proline (87125-48-2,91726-43-1,118492-87-8,335280-19-8)

Guidance literature:

for 6h;

DOI:10.1002/jlac.198319830611

Reference yield: 86.0%

(2R,3S)-3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (118449-01-7) → (3S)-1-(tert-butoxycarbonyl)-3-hydroxy-D-proline (118492-87-8,335280-19-8)

Guidance literature:

With potassium hydroxide; In methanol; water; for 16h; Ambient temperature;

DOI:10.1039/P19930001313

Reference yield: 78.0%

cis-3-acetoxy-N-(tert-butoxycarbonyl)-D-proline (118492-88-9) → (3S)-1-(tert-butoxycarbonyl)-3-hydroxy-D-proline (118492-87-8,335280-19-8)

Guidance literature:

With potassium hydroxide; In methanol; for 2h; Ambient temperature;

DOI:10.1002/hlca.19960790816

upstream raw materials:

cis-3-hydroxy-DL-proline

tert-butyl chloroformate

(2R,3S)-3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

cis-3-acetoxy-N-(tert-butoxycarbonyl)-D-proline

Downstream raw materials:

(2S,3R)-3-hydroxyproline

(3S)-1-(tert-butoxycarbonyl)-3-hydroxy-D-proline

cyclothialidine

(2S,3R)-1-[(tert-butoxy)carbonyl]-3-hydroxypyrrolidine-2-carboxylic acid

Refernces

• 1、 Cooper, Jeremy,Gallagher, Peter T.,Knight, David W.. "Expedient Synthesis of (+)-cis-(2R,3S)-3-Hydroxyproline and (-)-(1S,5S)-2-Oxa-6-azabicyclo octan-3-one (The Geissman-Waiss Lactone): Formal Enantioselective Syntheses of (-)-Retronecine and Related Pyrrolizidine Alkaloids". . p. 509 - 510. Retrieved 1988.
• 2、 Goetschi, Erwin,Jenny, Christian-Johannes,Reindl, Peter,Ricklin, Fabienne. "184. Total synthesis of cyclothialidine". . p. 2219 - 2234. Retrieved 2007/10/03.