methyl (R)-4,6-O-benzylidene-2,3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl (R)-4,6-O-benzylidene-2,3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside
• CAS No.: 220460-32-2
• Molecular Formula: C₁₈H₂₂O₅
• Molecular Weight: 318.37

Synonyms:methyl (R)-4,6-O-benzylidene-2,3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside

Chemical Property of methyl (R)-4,6-O-benzylidene-2,3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside

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Technology Process of methyl (R)-4,6-O-benzylidene-2,3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside

There total 2 articles about methyl (R)-4,6-O-benzylidene-2,3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside 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: 89.0%

methyl (R)-4,6-O-benzylidene-2-C-propenyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside (220460-30-0) → methyl (R)-4,6-O-benzylidene-2,3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside (220460-32-2)

Guidance literature:

Grubbs catalyst first generation; In benzene; at 60 ℃; for 17h;

DOI:10.1002/(SICI)1521-3773(19981217)37:23<3298::AID-ANIE3298>3.0.CO;2-O

Reference yield:

methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose (135700-48-0) → methyl (R)-4,6-O-benzylidene-2,3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside (220460-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / tetrahydrofuran / 2 h / Heating

2: 89 percent / Cl₂((C₆H₁₁)3P)2RuCHPh / benzene / 17 h / 60 °C

With Grubbs catalyst first generation; In tetrahydrofuran; benzene; 1: Addition / 2: Cyclization;

DOI:10.1021/jo991392z

Reference yield: 38.0%

methyl (R)-4,6-O-benzylidene-2,3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside (220460-32-2) → methyl (R)-4-O-benzoyl-6-C-bromo-2,3-C-(but-2-ene-1,4-diyl)-3,6-dideoxy-α-D-glucopyranoside (258326-55-5)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In chloroform; for 16h; Heating;

DOI:10.1021/jo991392z

upstream raw materials:

methyl (R)-4,6-O-benzylidene-2-C-propenyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside

methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

Downstream raw materials:

methyl (R)-4-O-benzoyl-6-C-bromo-2,3-C-(but-2-ene-1,4-diyl)-3,6-dideoxy-α-D-glucopyranoside

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