(1S,2R,3R,4S,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol

Base Information

Chemical Name:(1S,2R,3R,4S,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol
CAS No.:916599-83-2
Molecular Formula:C₃₃H₄₆O₆Si
Molecular Weight:566.81
Hs Code.:

Synonyms:(1S,2R,3R,4S,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol

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Chemical Property of (1S,2R,3R,4S,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol

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Technology Process of (1S,2R,3R,4S,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol

There total 6 articles about (1S,2R,3R,4S,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol 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:

: (1S,2S,4R,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-1-hydroxy-2-methyl-hept-6-en-3-one

: 916599-83-2
(1S,2R,3R,4S,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; diethyl ether; hexane; at -78 ℃; for 3h;
DOI:10.1021/ol062234e

Reference yield:

: 916599-82-1
(4R,5R)-4,5-Bis-benzyloxy-hept-6-en-3-one

: 916599-83-2
(1S,2R,3R,4S,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: chlorodicyclohexylborane; triethylamine / diethyl ether; hexane / 2 h / -78 °C

1.2: diethyl ether; hexane / 40 h / -15 °C

2.1: 11.0 g / LiBH₄ / diethyl ether; hexane; tetrahydrofuran / 3 h / -78 °C

With lithium borohydride; dicyclohexylboron chloride; triethylamine; In tetrahydrofuran; diethyl ether; hexane;
DOI:10.1021/ol062234e

Reference yield:

: 916599-91-2
(4S,5R)-4,5-Bis-benzyloxy-hept-6-en-3-ol

: 916599-83-2
(1S,2R,3R,4S,5R)-4,5-Bis-benzyloxy-1-[5-(tert-butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / molecular sieves 4 Angstroem; 4-methylmorpholine N-oxide; TPAP / CH₂Cl₂; acetonitrile / 0 - 20 °C

2.1: chlorodicyclohexylborane; triethylamine / diethyl ether; hexane / 2 h / -78 °C

2.2: diethyl ether; hexane / 40 h / -15 °C

3.1: 11.0 g / LiBH₄ / diethyl ether; hexane; tetrahydrofuran / 3 h / -78 °C

With lithium borohydride; tetrapropylammonium perruthennate; 4 A molecular sieve; dicyclohexylboron chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetonitrile;
DOI:10.1021/ol062234e