(1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol

Base Information

Chemical Name:(1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol
CAS No.:405915-17-5
Molecular Formula:C₂₈H₃₈O₅Si
Molecular Weight:482.692
Hs Code.:

Synonyms:(1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol

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Chemical Property of (1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol

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Technology Process of (1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol

There total 10 articles about (1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3-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: 48.0%

: 405914-77-4
tert-Butyl-diphenyl-[4-((1R,5S,7R)-7-vinyl-6,8-dioxa-bicyclo[3.2.1]oct-2-en-5-yl)-butoxy]-silane

: 405915-17-5
(1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol

: 405915-12-0
(1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-dihydroxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol

Guidance literature:: With osmium(VIII) oxide; (DHQ)2AQN; potassium hexacyanoferrate(III); potassium carbonate; In water; tert-butyl alcohol; at 20 ℃; for 60h;
DOI:10.1021/ol0172368

Reference yield:

: 405915-07-3
tert-Butyl-{4-[(4R,5R)-2-(3-chloro-propyl)-4,5-divinyl-[1,3]dioxolan-2-yl]-butoxy}-diphenyl-silane

: 405915-17-5
(1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 53 percent / potassium tert-butoxide; 18-crown-6 / hexane / 0.5 h / Heating

2.1: (Cy₃P)2(Cl)2Ru(=CHPh) / benzene / 2 h

2.2: 97 percent / Pb(OAc)4 / benzene

3.1: 48 percent / OsO₄; (DHQ)2AQN; K₃[Fe(CN)6] / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 60 h / 20 °C

With osmium(VIII) oxide; Grubbs catalyst first generation; (DHQ)2AQN; 18-crown-6 ether; potassium tert-butylate; potassium hexacyanoferrate(III); potassium carbonate; In hexane; water; tert-butyl alcohol; benzene; 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol0172368

Reference yield:

: 405914-82-1
[4-((4R,5R)-2-Allyl-4,5-divinyl-[1,3]dioxolan-2-yl)-butoxy]-tert-butyl-diphenyl-silane

: 405915-17-5
(1R,2R,3R,5S,7R)-5-[4-(tert-Butyl-diphenyl-silanyloxy)-butyl]-7-vinyl-6,8-dioxa-bicyclo[3.2.1]octane-2,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: (Cy₃P)2(Cl)2Ru(=CHPh) / benzene / 2 h

1.2: 97 percent / Pb(OAc)4 / benzene

2.1: 48 percent / OsO₄; (DHQ)2AQN; K₃[Fe(CN)6] / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 60 h / 20 °C

With osmium(VIII) oxide; Grubbs catalyst first generation; (DHQ)2AQN; potassium hexacyanoferrate(III); potassium carbonate; In water; tert-butyl alcohol; benzene; 2.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol0172368