(2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one}

Base Information

Chemical Name:(2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one}
CAS No.:893253-07-1
Molecular Formula:C₃₄H₄₈O₅S₃Si
Molecular Weight:661.036
Hs Code.:

(2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one}

Synonyms:(2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one}

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Chemical Property of (2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one}

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Technology Process of (2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one}

There total 1 articles about (2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one} 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: 61.0%

: 5418-86-0
tris(methylthio)methane

: 791839-27-5
(2S,5S,7S,10R)-spiro[7-(2-tert-butyldiphenylsilanyloxy)ethyl-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-[2,5]dihydrofuran[5]one]

: 893253-07-1
(2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one}

Guidance literature:: tris(methylthio)methane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(2S,5S,7S,10R)-spiro[7-(2-tert-butyldiphenylsilanyloxy)ethyl-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-[2,5]dihydrofuran[5]one]; In tetrahydrofuran; hexane; at -78 ℃; for 5h;
DOI:10.1021/ol0520018

Reference yield: 94.0%

: 893253-07-1
(2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one}

: 869631-54-9
(2S,5S,7S,10R,3'S)-spiro[7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-methyldihydrofuran-5-one]

Guidance literature:: With nickel; In tetrahydrofuran; water; for 6h;
DOI:10.1021/ol0520018

Reference yield:

: 893253-07-1
(2S,5S,7S,10R,3'S)-spiro{7-(2-tert-butyldiphenylsilanyloxyethyl)-5-methyl-1,6-dioxabicyclo[4.4.0]decane-2,2'-3-[tris(methylthio)methyl]dihydrofuran-5-one}

: 893269-03-9
C₃₉H₅₆O₆Si

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / Raney nickel / tetrahydrofuran; H₂O / 6 h

2: diisobutylaluminium hydride / CH₂Cl₂; hexane / 5 h / -78 °C

3: pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂; hexane / -78 - 20 °C

4: 209 mg / tin(IV) bromide / CH₂Cl₂ / 0.5 h / -78 °C

5: 65 percent / hydrofluoric acid / acetonitrile; H₂O / 2 h

With pyridine; dmap; hydrogen fluoride; stannic bromide; nickel; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/ol0520018