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

Base Information

Chemical Name:methyl (R)-4,6-O-benzylidene-2-O-pent-4-enyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside
CAS No.:258326-50-0
Molecular Formula:C₂₂H₃₀O₅
Molecular Weight:374.477
Hs Code.:

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

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Chemical Property of methyl (R)-4,6-O-benzylidene-2-O-pent-4-enyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside

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Technology Process of methyl (R)-4,6-O-benzylidene-2-O-pent-4-enyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside

There total 3 articles about methyl (R)-4,6-O-benzylidene-2-O-pent-4-enyl-3-deoxy-3-C-propenyl-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: 83.0%

: 1119-51-3
bromopentene

: 175021-62-2
methyl (R)-4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-glucopyranoside

: 258326-50-0
methyl (R)-4,6-O-benzylidene-2-O-pent-4-enyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; for 2h; Heating;
DOI:10.1021/jo991392z

Reference yield:

: 135700-48-0
methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

: 258326-50-0
methyl (R)-4,6-O-benzylidene-2-O-pent-4-enyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 50 percent / CeCl₃ / diethyl ether / 1.5 h / -40 °C

2: 83 percent / NaH / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Heating

With cerium(III) chloride; sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; 1: Addition / 2: Etherification;
DOI:10.1021/jo991392z

Reference yield:

: 171076-01-0
methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-3-C-propenyl-α-D-erythro-hexopyranoside

: 258326-50-0
methyl (R)-4,6-O-benzylidene-2-O-pent-4-enyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

2: 83 percent / NaH / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / Heating

With lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1: Reduction / 2: Etherification;
DOI:10.1021/jo991392z