methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside

Base Information

• Chemical Name: methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside
• CAS No.: 743422-32-4
• Molecular Formula: C₃₃H₄₄O₉
• Molecular Weight: 584.707

Synonyms:methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside

Chemical Property of methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside

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Technology Process of methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside

There total 2 articles about methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside 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: 58.0%

2,2:4,5-di-O-isopropylidene-D-arabinose (13039-93-5) + methyl 2,3-di-O-benzyl-5,6,7-trideoxy-7-(tri-n-butyl)stannyl-hept-5-(E)-eno-β-D-ribofuranoside → methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside (743422-31-3) + methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside (743422-32-4)

Guidance literature:

In dichloromethane; at 57 ℃; for 168h; under 9750780 Torr;

DOI:10.1016/j.tetasy.2004.04.020

Reference yield: 54.0%

2,2:4,5-di-O-isopropylidene-D-arabinose (13039-93-5) + methyl 2,3-di-O-benzyl-5,6,7-trideoxy-7-(tri-n-butyl)stannyl-hept-5-eno-β-D-ribofuranoside → methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5R)-vinyl-β-D-ribo-D-manno-deca-1,4-furanoside (743422-31-3) + methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside (743422-32-4)

Guidance literature:

In dichloromethane; at 57 ℃; for 168h; under 9750780 Torr;

DOI:10.1016/j.tetasy.2004.04.020

Reference yield: 79.0%

allyl bromide (106-95-6) + methyl 2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside (743422-32-4) → methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside (743422-35-7)

Guidance literature:

With sodium hydride; 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2004.04.020

upstream raw materials:

2,2:4,5-di-O-isopropylidene-D-arabinose

Downstream raw materials:

methyl 6-O-allyl-2,3-di-O-benzyl-5-deoxy-7,8:9,10-di-O-isopropylidene-(5S)-vinyl-β-D-ribo-D-gluco-deca-1,4-furanoside

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