3-((2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol

Base Information

• Chemical Name: 3-((2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol
• CAS No.: 887612-10-4
• Molecular Formula: C₃₄H₅₂O₄Si
• Molecular Weight: 552.87
• Mol file: 887612-10-4.mol

Synonyms:3-((2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol

Chemical Property of 3-((2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-((2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol

There total 16 articles about 3-((2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-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: 99.0%

C36H54O5Si → 3-((2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol (887612-10-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1002/chem.201102462

Reference yield:

(4R,5S,12S,15S)-1,4-Bis-benzyloxy-16-(tert-butyl-diphenyl-silanyloxy)-12-hydroxy-5,15-dimethyl-hexadec-6-yn-8-one → 3-((2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol (887612-10-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; for 12h; under 2585.74 Torr;

DOI:10.1021/ja057686l

Reference yield:

((E)-(2S,5S)-5-Benzyloxy-2-methyl-octa-3,7-dienyloxy)-tert-butyl-diphenyl-silane → 3-((2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol (887612-10-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 87 percent / Cl₂(Cy₃P)(IMes)Ru=CHPh / CH₂Cl₂ / 1.5 h / 40 °C

2.1: H₂ / Pd/C / ethyl acetate / 24 h

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

4.1: 0.746 g / H₂ / Pd/C / ethyl acetate; methanol / 12 h / 2585.74 Torr

With Cl₂(PCy₃)(N,N'-(Mes)2-imidazolidin-2-yl)Ru=CHC₆H₅; n-butyllithium; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate;

DOI:10.1021/ja057686l

upstream raw materials:

(2R,3R)-3,6-Bis-benzyloxy-2-methyl-hexanal

C₂₂H₂₈O₂

C₂₂H₂₆Br₂O₂

(3S,4R)-4,7-Bis-benzyloxy-3-methyl-heptane-1,2-diol

Downstream raw materials:

tert-butyl {(S)-4-[(2S,6S,8R,9S)-8-(3-iodopropyl)-9-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]-2-methylbutoxy}diphenylsilane

2-{3-[(2R,3S,6S,8S)-8-[(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutyl]-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]propyl}isoindoline-1,3-dione

bistramide A