(2S,3R,4R,5S,8S)-8-(m-benzyloxymethoxyphenyl)-8-methoxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)octane-1,4-diol

Base Information

• Chemical Name: (2S,3R,4R,5S,8S)-8-(m-benzyloxymethoxyphenyl)-8-methoxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)octane-1,4-diol
• CAS No.: 137531-88-5
• Molecular Formula: C₃₀H₄₄O₇
• Molecular Weight: 516.675
• Mol file: 137531-88-5.mol

Synonyms:(2S,3R,4R,5S,8S)-8-(m-benzyloxymethoxyphenyl)-8-methoxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)octane-1,4-diol

Chemical Property of (2S,3R,4R,5S,8S)-8-(m-benzyloxymethoxyphenyl)-8-methoxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)octane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S,8S)-8-(m-benzyloxymethoxyphenyl)-8-methoxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)octane-1,4-diol

There total 23 articles about (2S,3R,4R,5S,8S)-8-(m-benzyloxymethoxyphenyl)-8-methoxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)octane-1,4-diol 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: 62.0%

Methanesulfonic acid (2R,3R,4R,5S)-2-[(S)-3-(3-benzyloxymethoxy-phenyl)-3-methoxy-propyl]-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-methyl-5-(tetrahydro-pyran-2-yloxy)-hexyl ester → (2S,3R,4R,5S,8S)-8-(m-benzyloxymethoxyphenyl)-8-methoxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)octane-1,4-diol (137531-88-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 14h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

(2S,3S,4S,5S)-6-(tert-butyldimethylsiloxy)-2,3-epoxy-4-methyl-5-(2-tetrahydropyranyloxy)hexan-1-ol (137531-86-3) → (2S,3R,4R,5S,8S)-8-(m-benzyloxymethoxyphenyl)-8-methoxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)octane-1,4-diol (137531-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: CuI / tetrahydrofuran

2: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 12 h / Ambient temperature

3: 62 percent / lithium aluminum hydride / tetrahydrofuran / 14 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; copper(l) iodide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

C18H21BrMgO3 → (2S,3R,4R,5S,8S)-8-(m-benzyloxymethoxyphenyl)-8-methoxy-3,5-dimethyl-2-(2-tetrahydropyranyloxy)octane-1,4-diol (137531-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: CuI / tetrahydrofuran

2: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 12 h / Ambient temperature

3: 62 percent / lithium aluminum hydride / tetrahydrofuran / 14 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; copper(l) iodide; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)81547-7

upstream raw materials:

(2S,3R,4R,5R,8S)-8-(m-benzyloxymethoxyphenyl)-1-(tert-butyldimethylsiloxy)-5-hydroxymethyl-8-methoxy-3-methyl-2-(2-tetrahydropyranyloxy)octan-4-ol

3,4-dihydro-2H-pyran

Benzyloxymethyl chloride

3-hydroxy-trans-cinnamic acid

Downstream raw materials:

(2R,3R,4R,5S,8S)-8-(m-benzyloxymethylphenyl)-1,2-epoxy-8-methoxy-3,5-dimethyloctan-4-ol

(2R,3R,4R,5S,8S)-8--1,2-epoxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane

(2R,3R,8S,9S,10R,11S,14S)-14--1,2-isopropylidenedioxy-14-methoxy-10-(p-methoxybenzyloxy)-6,6-propylenedithio-3,5,5,9,11-pentamethyltetra-decan-8-ol

(3R,4R)-4-Benzyloxymethoxy-3-(4-methoxy-benzyloxy)-pentanoic acid (1S,2S,3R,4S,7S)-7-(3-benzyloxymethoxy-phenyl)-7-methoxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-[2-((R)-1,1,3-trimethyl-4-oxo-butyl)-[1,3]dithian-2-ylmethyl]-heptyl ester