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

Base Information

• Chemical Name: [(4R,5S,6S)-6-((S)-2-Benzyloxy-1-chloro-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-methanol
• CAS No.: 128308-21-4
• Molecular Formula: C₁₇H₂₅ClO₄
• Molecular Weight: 328.836
• Mol file: 128308-21-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

benzyl alcohol (100-51-6,185532-71-2) → [(4R,5S,6S)-6-((S)-2-Benzyloxy-1-chloro-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-methanol (128308-21-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / NaOMe / tetrahydrofuran / Ambient temperature

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

With tetrabutyl-ammonium chloride; sodium methylate; methanesulfonyl chloride; In tetrahydrofuran;

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

Reference yield:

(3aR,5S,6S,6aR)-5-((S)-2-Benzyloxy-1-chloro-ethyl)-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (128308-19-0) + 2,2-dimethoxy-propane (77-76-9) → [(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:

Yield given. Multistep reaction. Yields of byproduct given;

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

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

upstream raw materials:

(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

benzyl alcohol

Downstream raw materials:

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

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

(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