(2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane

Base Information

• Chemical Name: (2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane
• CAS No.: 858666-89-4
• Molecular Formula: C₂₈H₄₀O₄Si
• Molecular Weight: 468.709
• Mol file: 858666-89-4.mol

Synonyms:(2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane

Chemical Property of (2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane

There total 25 articles about (2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-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: 95.0%

(2S,5S,7S,1''S)-(+)-2-(1'-benzyloxymethyl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane (858666-87-2) → (2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane (858666-89-4)

Guidance literature:

With lithium 4,4′-di(tert-butyl)biphenyl; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ol0504291

Reference yield: 25.0%

(2S,5S,7S,1''S)-(+)-2-(1'-benzyloxymethyl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane (858666-87-2) → (2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane (858666-89-4) + (3S,6R,8S,1'S)-(+)-8-{(2'-tert-butyldiphenylsilyloxy)-1'-methylethyl}-3-hydroxy-1,7-dioxaspiro[5.5]undecane

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 4.5h;

DOI:10.1039/b600951d

Reference yield:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → (2S,5S,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-hydroxymethyl-1,6-dioxaspiro[4.5]decane (858666-89-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 70 percent / Ag₂O

2.1: AlMe₃ / CH₂Cl₂; hexane / 0.33 h / 0 °C

3.1: 1.14 g / camphorsulfonic acid / CH₂Cl₂ / 20 °C

4.1: tert-butyllithium / pentane; diethyl ether / 1.17 h / -78 - 0 °C

4.2: 72 percent / pentane; diethyl ether / 3 h / 0 °C

5.1: 92 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 20 °C / pH 7

6.1: 95 percent / liithium p,p'-di-tert-butylbiphenyl / tetrahydrofuran / -78 °C

With lithium 4,4′-di(tert-butyl)biphenyl; camphor-10-sulfonic acid; trimethylaluminum; tert.-butyl lithium; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; pentane;

DOI:10.1021/ol0504291

upstream raw materials:

(2S,5S,7S,1''S)-(+)-2-(1'-benzyloxymethyl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

(2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one

(5S,6S)-(+)-5-tert-butyldimethylsilyloxy-7-tert-butyldiphenylsilyloxy-6-methylheptan-1-al

(5S,6S)-(+)-5-tert-butyldimethylsilyloxy-7-tert-butyldiphenylsilyloxy-6-methylheptan-1-ol

Downstream raw materials:

3-((2S,3S)-3-{(2S,5S,7S)-7-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-1,6-dioxa-spiro[4.5]dec-2-yl}-2-methyl-oxiranyl)-2-hydroxy-propionic acid methyl ester

(2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-iodo-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane

(1'E,2S,5R,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(2'-ethoxycarbonyl-2'-methyl-1'-propenyl)-1,6-dioxaspiro[4.5]decane

(2S,5S,7S,1'S,2'S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(1',2'-epoxy-3'-hydroxy-2'-methylprop-1'-yl)-1,6-dioxaspiro[4.5]decane