(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)-2,3,5-trihydroxyundecanoic 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)-2,3,5-trihydroxyundecanoic acid γ-lactone
CAS No.:130860-96-7
Molecular Formula:C₃₁H₄₀O₁₁
Molecular Weight:588.652
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)-2,3,5-trihydroxyundecanoic 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)-2,3,5-trihydroxyundecanoic 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)-2,3,5-trihydroxyundecanoic 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)-2,3,5-trihydroxyundecanoic acid γ-lactone

There total 15 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)-2,3,5-trihydroxyundecanoic 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: 86.0%

: 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

: 130860-96-7
(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)-2,3,5-trihydroxyundecanoic acid γ-lactone

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 24h;
DOI:10.1021/jo00101a020

Reference yield:

: 130860-91-2
*,R^*)>-diethyl (2E,6E)-4,5-bis(phenylmethoxy)-2,6-octadienedioate

: 130860-96-7
(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)-2,3,5-trihydroxyundecanoic acid γ-lactone

Guidance literature:: Multi-step reaction with 13 steps

1: 71 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 18 h / Ambient temperature

2: 100 percent / 2,6-dimethyllutidine / CH₂Cl₂ / 14 h / Ambient temperature

3: 82 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

4: 1.) oxalyl chloride, DMSO / 1.) dichloromethane, -78 deg C, 15 min, 2.) dichloromethane, -78 deg C, 20 min

5: 82 percent / pyridine / toluene; tetrahydrofuran / 5 h / -78 - -10 °C

6: 95 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / -78 °C

7: 1.) oxalyl chloride, DMSO / 1.) dichlromethane, -78 deg C, 20 min, 2.) dichloromethane, -78 deg C, 1 h

8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, RT, 5 h

9: 86 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 0 °C

10: 88 percent / concd. H₂SO₄ / 18 h / Ambient temperature

11: 88 percent / dihydroquinine p-chlorobenzoate, N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 4 h / 0 °C

12: TFA / methanol / 60 h / Heating

13: H₂SO₄ / 48 h

With pyridine; 2,6-dimethyllutidine; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; dihydroquinine 4-chlorobenzoate; sulfuric acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene;

Reference yield:

: 130860-94-5
(2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate

: 130860-96-7
(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)-2,3,5-trihydroxyundecanoic acid γ-lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / dihydroquinine p-chlorobenzoate, N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 4 h / 0 °C

2: TFA / methanol / 60 h / Heating

3: H₂SO₄ / 48 h

With osmium(VIII) oxide; dihydroquinine 4-chlorobenzoate; sulfuric acid; 4-methylmorpholine N-oxide; trifluoroacetic acid; In methanol; water; acetone;