(2R,3R,4R,5S)-6-benzyloxy-3,5-dimethyl-1,2-O-isopropylidene-1,2,4-hexanetriol

Base Information

• Chemical Name: (2R,3R,4R,5S)-6-benzyloxy-3,5-dimethyl-1,2-O-isopropylidene-1,2,4-hexanetriol
• CAS No.: 128308-23-6
• Molecular Formula: C₁₈H₂₈O₄
• Molecular Weight: 308.418
• Mol file: 128308-23-6.mol

Synonyms:(2R,3R,4R,5S)-6-benzyloxy-3,5-dimethyl-1,2-O-isopropylidene-1,2,4-hexanetriol

Chemical Property of (2R,3R,4R,5S)-6-benzyloxy-3,5-dimethyl-1,2-O-isopropylidene-1,2,4-hexanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S)-6-benzyloxy-3,5-dimethyl-1,2-O-isopropylidene-1,2,4-hexanetriol

There total 14 articles about (2R,3R,4R,5S)-6-benzyloxy-3,5-dimethyl-1,2-O-isopropylidene-1,2,4-hexanetriol 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: 95.0%

{(1R,2S)-3-Benzyloxy-1-[(S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-2-methyl-propoxy}-tert-butyl-dimethyl-silane (128308-24-7) → (2R,3R,4R,5S)-6-benzyloxy-3,5-dimethyl-1,2-O-isopropylidene-1,2,4-hexanetriol (128308-23-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1271/bbb.62.599

Reference yield: 81.0%

lithium dimethylcuprate (15681-48-8) + (R)-4-[(S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranyl)-ethyl]-2,2-dimethyl-[1,3]dioxolane (128308-22-5) → (2R,3R,4R,5S)-6-benzyloxy-3,5-dimethyl-1,2-O-isopropylidene-1,2,4-hexanetriol (128308-23-6)

Guidance literature:

In diethyl ether; at -30 - 0 ℃; for 3h;

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

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → (2R,3R,4R,5S)-6-benzyloxy-3,5-dimethyl-1,2-O-isopropylidene-1,2,4-hexanetriol (128308-23-6)

Guidance literature:

Multi-step reaction with 6 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

5: 100 percent / NaOMe / methanol / 2 h / 0 - 40 °C

6: 81 percent / diethyl ether / 3 h / -30 - 0 °C

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

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

upstream raw materials:

lithium dimethylcuprate

(R)-4-[(S)-1-((2S,3R)-3-Benzyloxymethyl-oxiranyl)-ethyl]-2,2-dimethyl-[1,3]dioxolane

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

2,2-dimethoxy-propane

Downstream raw materials:

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

(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

{(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

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