8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-1,2,3-tri-O-benzoyl-D-glycero-D-galacto-β-D-galacto-undecopyranose

Base Information

Chemical Name:8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-1,2,3-tri-O-benzoyl-D-glycero-D-galacto-β-D-galacto-undecopyranose
CAS No.:130860-97-8
Molecular Formula:C₅₂H₅₄O₁₄
Molecular Weight:902.992
Hs Code.:

Synonyms:8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-1,2,3-tri-O-benzoyl-D-glycero-D-galacto-β-D-galacto-undecopyranose

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Chemical Property of 8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-1,2,3-tri-O-benzoyl-D-glycero-D-galacto-β-D-galacto-undecopyranose

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Technology Process of 8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-1,2,3-tri-O-benzoyl-D-glycero-D-galacto-β-D-galacto-undecopyranose

There total 17 articles about 8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-1,2,3-tri-O-benzoyl-D-glycero-D-galacto-β-D-galacto-undecopyranose 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: 34.0%

: 98-88-4
benzoyl chloride

: (2R,3R,4S,5R,6S)-6-[(1R,2R)-1,2-Bis-benzyloxy-2-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl]-tetrahydro-pyran-2,3,4,5-tetraol

: 130860-97-8
8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-1,2,3-tri-O-benzoyl-D-glycero-D-galacto-β-D-galacto-undecopyranose

Guidance literature:: In dichloromethane; at 0 ℃; for 1h;

Reference yield:

: 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

: 130860-97-8
8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-1,2,3-tri-O-benzoyl-D-glycero-D-galacto-β-D-galacto-undecopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) DIBAL-H, 2.) potassium sodium tartrate / 1.) dichloromethane, -90 deg C, 2 h, 2.) dichloromethane, acetone, water, overnight

2: 34 percent / CH₂Cl₂ / 1 h / 0 °C

With diisobutylaluminium hydride; Rochelle's salt; In dichloromethane;

Reference yield:

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

: 130860-97-8
8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-1,2,3-tri-O-benzoyl-D-glycero-D-galacto-β-D-galacto-undecopyranose

Guidance literature:: Multi-step reaction with 15 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

14: 1.) DIBAL-H, 2.) potassium sodium tartrate / 1.) dichloromethane, -90 deg C, 2 h, 2.) dichloromethane, acetone, water, overnight

15: 34 percent / CH₂Cl₂ / 1 h / 0 °C

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