(2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone

Base Information

Chemical Name:(2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone
CAS No.:166945-69-3
Molecular Formula:C₄₃H₆₈O₁₁Si₂
Molecular Weight:817.177
Hs Code.:

(2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone

Synonyms:(2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone

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Chemical Property of (2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone

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Technology Process of (2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone

There total 3 articles about (2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone 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: 77.0%

: (3R,4S,5S)-5-[(1R,2S,3R)-2,3-Bis-benzyloxy-1-hydroxy-3-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-propyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-ol

: 166945-69-3
(2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone

Guidance literature:: With 3 A molecular sieve; pyridinium chlorochromate; In dichloromethane; for 4h; Ambient temperature;
DOI:10.1021/jo00101a020

Reference yield:

: 166945-67-1
(2R,3S,4S,5R,6R,7R,8R,9S,10S,11R,12R)-8,9-Bis(benzyloxy)-4,5-bis<(tert-butyldimethylsilyl)oxy>-10,11:12,13-bis-O-(1-methylethylidene)-2,3,5,6-tridecanetetrol

: 166945-69-3
(2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone

Guidance literature:: Multi-step reaction with 2 steps

1: 76 percent / H₅IO₆ / tetrahydrofuran / 1 h / 0 °C

2: 77 percent / PCC, 3 Angstroem molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature

With 3 A molecular sieve; periodic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00101a020

Reference yield:

: (4S,8S,9R,10R,11R,12R)-8,9-Bis(benzyloxy)-4,5-bis<(tert-butyldimethylsilyl)oxy>-10,11:12,13-bis-O-(1-methylethylidene)-2,6-tridecadiene

: 166945-69-3
(2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-5-hydroxyundecanoic acid γ-lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / N-methylmorpholine N-oxide, aq. OsO₄ / acetone / 16 h / Ambient temperature

2: 76 percent / H₅IO₆ / tetrahydrofuran / 1 h / 0 °C

3: 77 percent / PCC, 3 Angstroem molecular sieves / CH₂Cl₂ / 4 h / Ambient temperature

With osmium(VIII) oxide; 3 A molecular sieve; 4-methylmorpholine N-oxide; periodic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetone;
DOI:10.1021/jo00101a020