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

Base Information

• Chemical Name: methyl (R)-4,6-O-benzylidene-2-C-methyl-2-O-propenyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside
• CAS No.: 258326-65-7
• Molecular Formula: C₂₁H₂₈O₅
• Molecular Weight: 360.45
• Mol file: 258326-65-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about methyl (R)-4,6-O-benzylidene-2-C-methyl-2-O-propenyl-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: 87.0%

allyl bromide (106-95-6) + methyl (R)-4,6-O-benzylidene-2-C-methyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside (258326-64-6) → methyl (R)-4,6-O-benzylidene-2-C-methyl-2-O-propenyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside (258326-65-7)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; for 2h; Heating;

DOI:10.1021/jo991392z

Reference yield:

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-3-C-propenyl-α-D-erythro-hexopyranoside (171076-01-0) → methyl (R)-4,6-O-benzylidene-2-C-methyl-2-O-propenyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside (258326-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 6 h / 0 - 20 °C

2: 87 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; diethyl ether; 1: Addition / 2: Etherification;

DOI:10.1021/jo991392z

Reference yield: 87.0%

methyl (R)-4,6-O-benzylidene-2-C-methyl-2-O-propenyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside (258326-65-7) → methyl (R)-4,6-O-benzylidene-2-methyl-2-O-3-C-(but-2-ene-1,4-diyl)-3-deoxy-α-D-glucopyranoside

Guidance literature:

With Grubbs catalyst first generation; In benzene; at 60 ℃; for 6h;

DOI:10.1021/jo991392z

upstream raw materials:

allyl bromide

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

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-3-C-propenyl-α-D-erythro-hexopyranoside