(R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one

Base Information

Chemical Name:(R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one
CAS No.:1063713-76-7
Molecular Formula:C₄₅H₈₂O₈Si₃
Molecular Weight:835.398
Hs Code.:

(R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one

Synonyms:(R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one

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Chemical Property of (R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one

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Technology Process of (R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one

There total 1 articles about (R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-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: 74.0%

: 1063693-69-5
(2S,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-carbaldehyde

: 1063713-65-4
5-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)hex-5-en-2-one

: 1063713-76-7
(R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one

: (S)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one

Guidance literature:: 5-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)hex-5-en-2-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Inert atmosphere;

(2S,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-carbaldehyde; In tetrahydrofuran; for 0.166667h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol801585j

Reference yield:

: 1063713-76-7
(R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one

: 917-54-4
methyllithium

: C₄₆H₈₆O₈Si₃

: 1063713-77-8
C₄₆H₈₆O₈Si₃

Guidance literature:: methyllithium; With titanium(IV) isopropylate; titanium tetrachloride; In tetrahydrofuran; diethyl ether; at 0 ℃; Inert atmosphere;

(R)-1-((2R,3R,5R)-5-((S)-1,2-bis(tert-butyldimethylsilyloxy)ethyl)-3-(tert-butyldimethylsilyloxy)-5-methyl-tetrahydrofuran-2-yl)-6-((2R,5R)-5-(benzyloxymethyl)-5-methyl-tetrahydrofuran-2-yl)-1-hydroxyhept-6-en-3-one; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol801585j