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

Base Information

• Chemical Name: (2E,3S,4S,5S)-4-benzyloxy-3-(tert-butyldiphenylsiloxy)-2-methoxycarbonylmethylidene-1,6-dioxaspiro[4.5]decane
• CAS No.: 862014-03-7
• Molecular Formula: C₃₄H₄₀O₆Si
• Molecular Weight: 572.774
• Mol file: 862014-03-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(3R,4S)-4-Benzyloxy-3-(tert-butyl-diphenyl-silanyloxy)-9-hydroxy-non-1-yn-5-one + methanol (67-56-1) + carbon monoxide (201230-82-2) → {(R)-1-[(S)-Benzyloxy-(2-methoxy-tetrahydro-pyran-2-yl)-methyl]-prop-2-ynyloxy}-tert-butyl-diphenyl-silane + (2E,3S,4S,5S)-4-benzyloxy-3-(tert-butyldiphenylsiloxy)-2-methoxycarbonylmethylidene-1,6-dioxaspiro[4.5]decane (862014-03-7)

Guidance literature:

With p-benzoquinone; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; at 20 ℃; for 48h; under 760 Torr;

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)-4-benzyloxy-3-(tert-butyldiphenylsiloxy)-2-(2-hydroxyethylidene)-1,6-dioxaspiro[4.5]decane

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.5h;

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) → [(3S,4S,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxy-1,6-dioxa-spiro[4.5]dec-(2E)-ylidene]-acetaldehyde

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: manganese dioxide / CH₂Cl₂ / 1 h / 20 °C

With manganese(IV) oxide; 4,4'-di-tert-butylbiphenyl; lithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo050822k

upstream raw materials:

methanol

carbon monoxide

Downstream raw materials:

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

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