D-Proline, 2-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl )-1-[(4-methoxyphenyl)methyl]-3-methyl-5-oxo-, methyl ester, (3S,4R)-

Base Information

• Chemical Name: D-Proline, 2-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl )-1-[(4-methoxyphenyl)methyl]-3-methyl-5-oxo-, methyl ester, (3S,4R)-
• CAS No.: 704910-41-8
• Molecular Formula: C24H33NO7
• Molecular Weight: 447.529
• Mol file: 704910-41-8.mol

Synonyms:

Chemical Property of D-Proline, 2-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl )-1-[(4-methoxyphenyl)methyl]-3-methyl-5-oxo-, methyl ester, (3S,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Proline, 2-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl )-1-[(4-methoxyphenyl)methyl]-3-methyl-5-oxo-, methyl ester, (3S,4R)-

There total 6 articles about D-Proline, 2-[(S)-(1S)-2-cyclohexen-1-ylhydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl )-1-[(4-methoxyphenyl)methyl]-3-methyl-5-oxo-, methyl ester, (3S,4R)- 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: 92.0%

(3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester (704910-39-4) → (2R,3S,4R)-2-[(S)-{(S)-cyclohex-2-enyl}hydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl)-1-(4-methoxybenzyl)-3-methyl-5-oxopyrrolidine-2-carboxylic acid methyl ester (704910-41-8)

Guidance literature:

With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate; In tetrahydrofuran; methanol; at 23 ℃; for 18h;

DOI:10.1021/ja048613p

Reference yield: 60.0%

(3aR,6R,6aS)-6-[(S)-{(S)-cyclohex-2-enyl}hydroxymethyl]-5-(4-methoxybenzyl)-6a-methyl-2,4-dioxohexahydrofuro[2,3-c]pyrrole-6-carboxylic acid methyl ester (1055312-51-0) → (2R,3S,4R)-2-[(S)-{(S)-cyclohex-2-enyl}hydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl)-1-(4-methoxybenzyl)-3-methyl-5-oxopyrrolidine-2-carboxylic acid methyl ester (704910-41-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 18h;

DOI:10.1016/j.tet.2008.06.038

Reference yield:

methyl (2R)-1-(4-methoxybenzyl)-2-((benzyloxy)methyl)-3-hydroxy-3-methyl-4-methylene-5-oxopyrrolidine-2-carboxaldehyde → (2R,3S,4R)-2-[(S)-{(S)-cyclohex-2-enyl}hydroxymethyl]-3-hydroxy-4-(2-hydroxyethyl)-1-(4-methoxybenzyl)-3-methyl-5-oxopyrrolidine-2-carboxylic acid methyl ester (704910-41-8)

Guidance literature:

Multi-step reaction with 6 steps

1: DMAP; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 89 percent / tributyltin hydride; AIBN / benzene / 4 h / 80 °C

3: H₂ / Pd/C / ethanol / 12 h / 23 °C / 760 Torr

4: 2.68 g / Dess-Martin reagent / CH₂Cl₂ / 1 h / 23 °C

5: 83 percent / tetrahydrofuran / 5 h / -78 °C

6: 92 percent / KHCO₃; KF; aq. H₂O₂ / methanol; tetrahydrofuran / 18 h / 23 °C

With dmap; potassium fluoride; 2,2'-azobis(isobutyronitrile); hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; potassium hydrogencarbonate; Dess-Martin periodane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; benzene; 4: Dess-Martin oxidation / 6: Tamao-Fleming oxidation;

DOI:10.1021/ja048613p

upstream raw materials:

(3R,3aS,7aR)-3-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

(3S,3aS,7aR)-3-Formyl-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

(3R,3aS,7aR)-3-Benzyloxymethyl-2-(4-methoxy-benzyl)-3a,5,5-trimethyl-1-oxo-octahydro-4-oxa-2-aza-5-sila-indene-3-carboxylic acid methyl ester

(2R,3S)-2-Benzyloxymethyl-3-(bromomethyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyl)-3-methyl-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

Downstream raw materials:

(2R,3S,4R)-2-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-3-hydroxy-4-(2-hydroxy-ethyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid

salinosporamide A

(2R,3S,4R)-2-((S)-(S)-Cyclohex-2-enyl-hydroxy-methyl)-3-hydroxy-4-(2-hydroxy-ethyl)-3-methyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester