Acetic acid (1S,2R,3R,5S,7R)-2-acetoxy-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-diacetoxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

Base Information

Chemical Name:Acetic acid (1S,2R,3R,5S,7R)-2-acetoxy-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-diacetoxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester
CAS No.:405915-24-4
Molecular Formula:C₃₆H₄₈O₁₁Si
Molecular Weight:684.856
Hs Code.:

Synonyms:Acetic acid (1S,2R,3R,5S,7R)-2-acetoxy-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-diacetoxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

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Chemical Property of Acetic acid (1S,2R,3R,5S,7R)-2-acetoxy-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-diacetoxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

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Technology Process of Acetic acid (1S,2R,3R,5S,7R)-2-acetoxy-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-diacetoxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

There total 12 articles about Acetic acid (1S,2R,3R,5S,7R)-2-acetoxy-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-diacetoxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester 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: 99.0%

: 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

: 108-24-7
acetic anhydride

: 405915-24-4
Acetic acid (1S,2R,3R,5S,7R)-2-acetoxy-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-diacetoxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

Guidance literature:: With pyridine; dmap; In dichloromethane; for 1h;
DOI:10.1021/ol0172368

Reference yield:

: 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

: 405915-24-4
Acetic acid (1S,2R,3R,5S,7R)-2-acetoxy-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-diacetoxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 48 percent / OsO₄; (DHQ)2AQN; K₃[Fe(CN)6] / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 60 h / 20 °C

2: 66 percent / OsO₄; (DHQ)2AQN; K₃[Fe(CN)6] / K₂CO₃ / 2-methyl-propan-2-ol; H₂O

3: 99 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 1 h

With pyridine; dmap; osmium(VIII) oxide; (DHQ)2AQN; potassium hexacyanoferrate(III); potassium carbonate; In dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 2: 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

: 405915-24-4
Acetic acid (1S,2R,3R,5S,7R)-2-acetoxy-5-[4-(tert-butyl-diphenyl-silanyloxy)-butyl]-7-((R)-1,2-diacetoxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

Guidance literature:: Multi-step reaction with 4 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

3.1: 66 percent / OsO₄; (DHQ)2AQN; K₃[Fe(CN)6] / K₂CO₃ / 2-methyl-propan-2-ol; H₂O

4.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 1 h

With pyridine; dmap; osmium(VIII) oxide; Grubbs catalyst first generation; (DHQ)2AQN; potassium hexacyanoferrate(III); potassium carbonate; In dichloromethane; water; tert-butyl alcohol; benzene; 2.1: Sharpless asymmetric dihydroxylation / 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol0172368