methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside

Base Information

• Chemical Name: methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside
• CAS No.: 119007-14-6
• Molecular Formula: C₆₈H₆₈O₁₃
• Molecular Weight: 1093.28

Synonyms:methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside

Chemical Property of methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside

There total 11 articles about methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside 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: 36.0%

benzoyl chloride (98-88-4) + (2S,3R,4S,5R)-2-((1R,2S,3S,4R,5R)-1,2,3,4,5,6-Hexakis-benzyloxy-hexyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol (99212-56-3,119007-12-4) → methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-α-D-galacto-undecapyranoside (99212-57-4) + methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside (119007-14-6)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/ja00188a038

Reference yield:

1-[2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydro-di[1,3]dioxolo[5,4-b:5,4-d]pyran-5-yl]-(1R)-but-3-en-1-ol (99166-42-4) → methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside (119007-14-6)

Guidance literature:

Multi-step reaction with 11 steps

1: NaH / dimethylformamide

2: 1.) O₃; 2.) Zn, AcOH / 1.) CH₂Cl₂, -78 deg C

3: Et₃N, DMAP / CH₂Cl₂

4: 1.) O₃; 2.) Zn, AcOH / 1.) CH₂Cl₂

5: 75 percent / MgBr₂ / CH₂Cl₂; toluene / 0 °C

6: 95 percent / NaBH₄, CeCl₃

7: 2.) K₂CO₃ / 2.) CH₃OH

8: LiBH₄ / tetrahydrofuran / Heating

9: NaH / dimethylformamide

10: methanolic HCl / methanol

11: pyridine

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; sodium hydride; potassium carbonate; ozone; acetic acid; triethylamine; magnesium bromide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00311a090

Reference yield:

(3aR,5R,5aS,8aS,8bR)-5-((R)-1-Benzyloxy-but-3-enyl)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (99166-43-5) → methyl 2,3-di-O-benzoyl-6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside (119007-14-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) O₃; 2.) Zn, AcOH / 1.) CH₂Cl₂, -78 deg C

2: Et₃N, DMAP / CH₂Cl₂

3: 1.) O₃; 2.) Zn, AcOH / 1.) CH₂Cl₂

4: 75 percent / MgBr₂ / CH₂Cl₂; toluene / 0 °C

5: 95 percent / NaBH₄, CeCl₃

6: 2.) K₂CO₃ / 2.) CH₃OH

7: LiBH₄ / tetrahydrofuran / Heating

8: NaH / dimethylformamide

9: methanolic HCl / methanol

10: pyridine

With pyridine; hydrogenchloride; dmap; sodium tetrahydroborate; lithium borohydride; cerium(III) chloride; sodium hydride; potassium carbonate; ozone; acetic acid; triethylamine; magnesium bromide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00311a090

upstream raw materials:

benzoyl chloride

(2S,3R,4S,5R)-2-((1R,2S,3S,4R,5R)-1,2,3,4,5,6-Hexakis-benzyloxy-hexyl)-6-methoxy-tetrahydro-pyran-3,4,5-triol

1-[2,2,7,7-tetramethyl-(3aR,5R,5aS,8aS,8bR)-perhydro-di[1,3]dioxolo[5,4-b:5,4-d]pyran-5-yl]-(1R)-but-3-en-1-ol

(3aR,5R,5aS,8aS,8bR)-5-((R)-1-Benzyloxy-but-3-enyl)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

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