(2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decan-4-ol

Base Information

• Chemical Name: (2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decan-4-ol
• CAS No.: 862014-04-8
• Molecular Formula: C₂₆H₃₄O₅Si
• Molecular Weight: 454.638
• Mol file: 862014-04-8.mol

Synonyms:(2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decan-4-ol

Chemical Property of (2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decan-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decan-4-ol

There total 3 articles about (2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decan-4-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:

(2E,3S,4S,5S)-4-benzyloxy-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decane → (2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decan-4-ol (862014-04-8)

Guidance literature:

With 4,4'-di-tert-butylbiphenyl; lithium; In tetrahydrofuran; at -78 ℃; for 0.166667h;

DOI:10.1021/jo050822k

Reference yield:

(3R,4S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-non-1-yn-5-one → (2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decan-4-ol (862014-04-8)

Guidance literature:

Multi-step reaction with 3 steps

1: p-benzoquinone / Pd₂(dba)3*CHCl₃ / 48 h / 20 °C / 760 Torr

2: diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

3: lithium; p,p'-di-tert-butylbiphenyl / tetrahydrofuran / 0.17 h / -78 °C

With 4,4'-di-tert-butylbiphenyl; lithium; diisobutylaluminium hydride; p-benzoquinone; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo050822k

Reference yield:

(2E,3S,4S,5S)-4-benzyloxy-3-(tert-butyldiphenylsiloxy)-2-methoxycarbonylmethylidene-1,6-dioxaspiro[4.5]decane (862014-03-7) → (2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decan-4-ol (862014-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / -78 °C

2: lithium; p,p'-di-tert-butylbiphenyl / tetrahydrofuran / 0.17 h / -78 °C

With 4,4'-di-tert-butylbiphenyl; lithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo050822k

upstream raw materials:

(2E,3S,4S,5S)-4-benzyloxy-3-(tert-butyldiphenylsiloxy)-2-methoxycarbonylmethylidene-1,6-dioxaspiro[4.5]decane

Downstream raw materials:

(2E,3S,4S,5S)-3-(tert-butyldiphenylsiloxy)-2-propynylidene-1,6-dioxaspiro[4.5]decan-4-ol