(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

Base Information

Chemical Name:(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
CAS No.:887001-90-3
Molecular Formula:C₃₁H₄₄O₅Si
Molecular Weight:524.773
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 28 articles about (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 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%

: 858666-93-0
(1'E,2S,5R,7S,1''S)-(+)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-2-(3'-hydroxy-1'-propenyl)-1,6-dioxaspiro[4.5]decane

: 887001-90-3
(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

Guidance literature:: With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tert.-butylhydroperoxide; In dichloromethane; at -23 ℃; for 12h;
DOI:10.1021/ol0504291

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 887001-90-3
(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

Guidance literature:: Multi-step reaction with 10 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

7.1: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 3 h

8.1: 86 percent / CH₂Cl₂ / 2 h / 20 °C

9.1: 89 percent / Dibal-H / CH₂Cl₂; hexane / 1 h / -40 °C

10.1: 95 percent / molecular sieves 4 Angstroem; L-(+)-diethyl tartrate; titanium isopropoxide / tert-butyl hydroperoxide / CH₂Cl₂ / 12 h / -23 °C

With pyridine; titanium(IV) isopropylate; lithium 4,4′-di(tert-butyl)biphenyl; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; trimethylaluminum; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; tert.-butylhydroperoxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; pentane; 8.1: Wittig reaction;
DOI:10.1021/ol0504291

Reference yield:

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

: 887001-90-3
(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

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

2: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

3: 99 percent / CH₂Cl₂ / 20 h / 20 °C

4: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

5: 71 percent / 4 Angstroem molecular sieves; (+)-diethyl L-tartrate; tert-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 4 h / -20 °C

With pyridine; tert.-butylhydroperoxide; diisobutylaluminum hydride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; hydrogen; Dess-Martin periodane; titanium(IV) isopropylate; palladium on activated charcoal; In dichloromethane; ethyl acetate; toluene; 3: Wittig olefination;
DOI:10.1039/b600951d