methyl 2,3,4-tri-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside
• CAS No.: 869641-98-5
• Molecular Formula: C₃₆H₃₈O₇
• Molecular Weight: 582.694

Synonyms:methyl 2,3,4-tri-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside

Chemical Property of methyl 2,3,4-tri-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside

Chemical Property:

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Technology Process of methyl 2,3,4-tri-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside

There total 2 articles about methyl 2,3,4-tri-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside 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: 95.0%

methyl 3,4-di-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside (869641-97-4) + benzyl bromide (100-39-0) → methyl 2,3,4-tri-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside (869641-98-5)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/ol051912e

Reference yield:

1,6-anhydro-3,4-di-O-benzyl-5,7-O-benzylidene-2-deoxy-D-glycero-D-gulosept-1-enitol → methyl 2,3,4-tri-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside (869641-98-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMDO / CH₂Cl₂ / 1 h / 0 °C

1.2: 68 percent / methanol / 120 h / 20 °C

2.1: 95 percent / NaH / dimethylformamide / 20 °C

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

DOI:10.1021/ol051912e

Reference yield: 61.0%

methyl 2,3,4-tri-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside (869641-98-5) → methyl 2,3,4,7-tetra-O-benzyl-β-D-glycero-D-guloseptanoside

Guidance literature:

With dimethylamine borane; boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 1.5h;

DOI:10.1021/ol051912e

upstream raw materials:

methyl 3,4-di-O-benzyl-5,7-O-benzylidene-β-D-glycero-D-guloseptanoside

benzyl bromide

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