methyl 6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-α-D-galacto-undecapyranoside

Base Information

Chemical Name:methyl 6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-α-D-galacto-undecapyranoside
CAS No.:99212-56-3
Molecular Formula:C₅₄H₆₀O₁₁
Molecular Weight:885.064
Hs Code.:

Synonyms:methyl 6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-α-D-galacto-undecapyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl 6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-α-D-galacto-undecapyranoside

Chemical Property:

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Technology Process of methyl 6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-α-D-galacto-undecapyranoside

There total 11 articles about methyl 6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-α-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: 14.0%

: 67-56-1
methanol

: 99212-55-2
6,7,8,9,10,11-hexa-O-benzyl-1,2,3,4-di-O-isopropylidene-D-glycero-D-galacto-D-galacto-undecapyranose

: 118893-80-4,119007-13-5
(2R,3R,4R)-2-((1R,2S,3R,4S,5R,6R)-2,3,4,5,6,7-Hexakis-benzyloxy-1-hydroxy-heptyl)-5-methoxy-tetrahydro-furan-3,4-diol

: 99212-56-3
methyl 6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-α-D-galacto-undecapyranoside

: 119007-12-4
methyl 6,7,8,9,10,11-hexa-O-benzyl-D-glycero-D-galacto-β-D-galacto-undecapyranoside

Guidance literature:: With hydrogenchloride; at 75 ℃; for 8h; Yield given. Yields of byproduct given;
DOI:10.1021/ja00188a038

Reference yield:

: 99166-42-4
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

: 99212-56-3,119007-12-4
(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

Guidance literature:: Multi-step reaction with 10 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

With 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:

: 99166-43-5
(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

: 99212-56-3,119007-12-4
(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

Guidance literature:: Multi-step reaction with 9 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

With 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