(2S,3S,4R)-1-Benzyloxy-2-chloro-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-3-ol

Base Information

• Chemical Name: (2S,3S,4R)-1-Benzyloxy-2-chloro-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-3-ol
• CAS No.: 128308-20-3
• Molecular Formula: C₁₇H₂₅ClO₄
• Molecular Weight: 328.836
• Mol file: 128308-20-3.mol

Synonyms:(2S,3S,4R)-1-Benzyloxy-2-chloro-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-3-ol

Chemical Property of (2S,3S,4R)-1-Benzyloxy-2-chloro-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-1-Benzyloxy-2-chloro-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-3-ol

There total 5 articles about (2S,3S,4R)-1-Benzyloxy-2-chloro-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-3-ol 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: 91.0%

[(4R,5S,6S)-6-((S)-2-Benzyloxy-1-chloro-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-methanol (128308-21-4) → (2S,3S,4R)-1-Benzyloxy-2-chloro-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-3-ol (128308-20-3)

Guidance literature:

toluene-4-sulfonic acid; In acetone; Ambient temperature;

DOI:10.1016/S0040-4039(00)70660-5

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (2S,3S,4R)-1-Benzyloxy-2-chloro-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-3-ol (128308-20-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / NaOMe / tetrahydrofuran / Ambient temperature

2: 1.) MsCl; 2.) n-Bu₄NCl / 1.) pyridine; 2.) benzene, reflux

4: 91 percent / TsOH / acetone / Ambient temperature

With tetrabutyl-ammonium chloride; sodium methylate; methanesulfonyl chloride; toluene-4-sulfonic acid; In tetrahydrofuran; acetone;

DOI:10.1016/S0040-4039(00)70660-5

Reference yield:

6-O-benzyl-3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-allofuranose (114144-67-1) → (2S,3S,4R)-1-Benzyloxy-2-chloro-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-pentan-3-ol (128308-20-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) MsCl; 2.) n-Bu₄NCl / 1.) pyridine; 2.) benzene, reflux

3: 91 percent / TsOH / acetone / Ambient temperature

With tetrabutyl-ammonium chloride; methanesulfonyl chloride; toluene-4-sulfonic acid; In acetone;

DOI:10.1016/S0040-4039(00)70660-5

upstream raw materials:

[(4R,5S,6S)-6-((S)-2-Benzyloxy-1-chloro-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-methanol

(3aR,5S,6S,6aR)-5-((S)-2-Benzyloxy-1-chloro-ethyl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

2,2-dimethoxy-propane

6-O-benzyl-3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-allofuranose

Downstream raw materials:

{(1R,2S,5S)-5-(3-Benzyloxy-phenyl)-1-[(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-5-methoxy-2-methyl-pentyloxy}-tert-butyl-dimethyl-silane

(4S,5R,6S)-1-(3-Benzyloxy-phenyl)-5-(tert-butyl-dimethyl-silanyloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-heptan-1-one

3-[(1S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-methoxy-4-methyl-heptyl]-phenol

{(1R,2S)-3-Benzyloxy-1-[(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-2-methyl-propoxy}-tert-butyl-dimethyl-silane