2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylcyclopentanol

Base Information

• Chemical Name: 2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylcyclopentanol
• CAS No.: 911218-24-1
• Molecular Formula: C₂₆H₃₈O₃Si
• Molecular Weight: 426.671

Synonyms:2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylcyclopentanol

Chemical Property of 2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylcyclopentanol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylcyclopentanol

There total 2 articles about 2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylcyclopentanol 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: 74.0%

2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylenecyclopentanol (911218-26-3) → 2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylcyclopentanol (911218-24-1)

Guidance literature:

With Crabtree's catalyst; hydrogen; In dichloromethane; cooling;

DOI:10.1021/ol0615230

Reference yield:

3-benzyloxymethyl-2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-methylenecyclopentanol (911218-23-0) → 2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylcyclopentanol (911218-24-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / BCl₃ / CH₂Cl₂; heptane / 0.5 h / -40 °C

2: 74 percent / [Ir(cod)py(PCy₃)]PF₆; H₂ / CH₂Cl₂ / cooling

With Crabtree's catalyst; hydrogen; boron trichloride; In n-heptane; dichloromethane;

DOI:10.1021/ol0615230

Reference yield: 95.0%

2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylcyclopentanol (911218-24-1) + (4S,6S)-5-Eth-(E)-ylidene-4-[2-oxo-2-(2,4,6-trichloro-benzoyloxy)-ethyl]-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester → 4-{2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-hydroxycarbonylmethyl-5-methylcyclopentylmethoxycarbonylmethyl}-bis-[5-ethylidene-6-(3,4,5-triacetoxy-6-acetoxymethyltetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester]

Guidance literature:

With dmap; In dichloromethane; at 0 - 20 ℃; for 2.16667h;

DOI:10.1021/ol0615230

upstream raw materials:

2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-3-hydroxymethyl-4-methylenecyclopentanol

3-benzyloxymethyl-2-[2-(tert-butyldiphenylsilanyloxy)-1-methyl-ethyl]-4-methylenecyclopentanol

Downstream raw materials:

4-{2-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-hydroxy-5-methylcyclopentylmethoxycarbonylmethyl}-5-ethylidene-6-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

5-ethylidene-4-[3-hydroxy-2-(2-hydroxy-1-methyl-ethyl)-5-methylcyclopentylmethoxycarbonylmethyl]-6-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-2-yloxy)-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester

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