3,6-di-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexopyranos-6-yl)-1,2-O-isopropylidene-L-glycero-β-L-ido-hexo-1,4-furanose

Base Information

• Chemical Name: 3,6-di-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexopyranos-6-yl)-1,2-O-isopropylidene-L-glycero-β-L-ido-hexo-1,4-furanose
• CAS No.: 120403-16-9
• Molecular Formula: C₃₅H₄₆O₁₂
• Molecular Weight: 658.743

Synonyms:

Chemical Property of 3,6-di-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexopyranos-6-yl)-1,2-O-isopropylidene-L-glycero-β-L-ido-hexo-1,4-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-di-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexopyranos-6-yl)-1,2-O-isopropylidene-L-glycero-β-L-ido-hexo-1,4-furanose

There total 2 articles about 3,6-di-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexopyranos-6-yl)-1,2-O-isopropylidene-L-glycero-β-L-ido-hexo-1,4-furanose 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: 55.0%

5,6-anhydro-3-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hextopyranos-6-yl)-1,2-O-isopropylidene-D-glycero-β-L-ido-hexo-1,4-furanose (120403-15-8,120444-45-3) + benzyl alcohol (100-51-6,185532-71-2) → 3,6-di-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexopyranos-6-yl)-1,2-O-isopropylidene-L-glycero-β-L-ido-hexo-1,4-furanose (120403-16-9)

Guidance literature:

With titanium(IV) isopropylate; for 30h; Heating;

DOI:10.1016/0008-6215(88)84076-X

Reference yield:

3-O-benzyl-5-deoxy-5-C-<(E)-7-deoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranos-7-ylidene>-1,2-O-isopropylidene-α-D-xylofuranose (115259-73-9,115304-53-5) → 3,6-di-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexopyranos-6-yl)-1,2-O-isopropylidene-L-glycero-β-L-ido-hexo-1,4-furanose (120403-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 61.2 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 24 h / Ambient temperature

2: 55 percent / titanium tetraisopropoxide / 30 h / Heating

With titanium(IV) isopropylate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/0008-6215(88)84076-X

Reference yield:

1-bromo-butane (109-65-9) + 3,6-di-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexopyranos-6-yl)-1,2-O-isopropylidene-L-glycero-β-L-ido-hexo-1,4-furanose (120403-16-9) → (3aR,5R,5aS,8aS,8bR)-5-[(1R,2R,3S)-2-Benzyloxy-3-((3aR,5R,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1,3-dibutoxy-propyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(88)84076-X

upstream raw materials:

5,6-anhydro-3-O-benzyl-6-C-(1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hextopyranos-6-yl)-1,2-O-isopropylidene-D-glycero-β-L-ido-hexo-1,4-furanose

benzyl alcohol

3-O-benzyl-5-deoxy-5-C-<(E)-7-deoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-heptopyranos-7-ylidene>-1,2-O-isopropylidene-α-D-xylofuranose

Downstream raw materials:

Acetic acid (1R,2R,3S)-3-acetoxy-2-benzyloxy-3-((3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-1-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-propyl ester

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