[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester
• CAS No.: 634587-10-3
• Molecular Formula: C₃₀H₅₁NO₅
• Molecular Weight: 505.739
• Mol file: 634587-10-3.mol

Synonyms:[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester

Chemical Property of [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester

There total 11 articles about [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester 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: 86.0%

[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester (634587-07-8) → [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester (634587-10-3)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;

DOI:10.1002/anie.200454215

Reference yield:

{(Z)-(S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-heptadec-2-enyl}-carbamic acid benzyl ester (634586-98-4) → [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester (634587-10-3)

Guidance literature:

Multi-step reaction with 3 steps

1: AD-mix-β

2: 95 percent / pyridinium p-toluenesulfonate / CH₂Cl₂

3: 86 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran

With AD-mix-β; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; In tetrahydrofuran; dichloromethane; 1: Sharpless dihydroxylation;

DOI:10.1002/anie.200454215

Reference yield:

L-2-[(benzyloxycarbonyl)amino]-4-(tert-butyldimethylsilyloxy)-butylaldehyde (634586-95-1) → [(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-carbamic acid benzyl ester (634587-10-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / tetrahydrofuran

2: AD-mix-β

3: 95 percent / pyridinium p-toluenesulfonate / CH₂Cl₂

4: 86 percent / tetrabutylammonium fluoride; acetic acid / tetrahydrofuran

With AD-mix-β; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; acetic acid; In tetrahydrofuran; dichloromethane; 2: Sharpless dihydroxylation;

DOI:10.1002/anie.200454215

upstream raw materials:

[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester

L-2-[(benzyloxycarbonyl)amino]-4-(tert-butyldimethylsilyloxy)-butylaldehyde

{(Z)-(S)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-heptadec-2-enyl}-carbamic acid benzyl ester

(3S,4S,5R)-1-O-(tert-butyldimethylsilyl)-3-[(benzyloxycarbonyl)amino]-4,5-nonadecanediol

Downstream raw materials:

[(S)-1-((4S,5R)-2,2-Dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-3-iodo-propyl]-carbamic acid benzyl ester

Benzoic acid (2R,3S,4R,5R,6S)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2-oxo-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-diisopropylsilanyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Benzoic acid (2R,3S,4R,5S,6R)-6-[(S)-3-(benzyl-benzyloxycarbonyl-amino)-3-((4S,5R)-2-oxo-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-4,5-bis-benzyloxy-3-(fluoro-diisopropyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl ester

Benzyl-[(S)-3-[(2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-6-sulfonyl]-1-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-propyl]-carbamic acid benzyl ester