methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside

Base Information

• Chemical Name: methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside
• CAS No.: 104107-39-3
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.445
• Mol file: 104107-39-3.mol

Synonyms:methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside

Chemical Property of methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside

There total 1 articles about methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside 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: 98.0%

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside (5987-36-0) + benzyl bromide (100-39-0) → methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside (104107-39-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1) r.t., 1 h, 2) r.t., 2 h;

DOI:10.1246/bcsj.58.3457

Reference yield: 83.0%

methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside (104107-39-3) → methyl 2-O-benzyl-3-deoxy-3-C-methyl-α-D-altropyranoside (104107-40-6)

Guidance literature:

With dichloro-acetic acid; at 0 ℃; for 0.5h;

DOI:10.1246/bcsj.58.3457

Reference yield:

methyl 2-O-benzyl-4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside (104107-39-3) → 2-O-acetyl-3-O-benzyl-1,4,7-trideoxy-5,6-O-isopropylidene-4-C-methyl-D-glycero-D-gluco-heptitol

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / 75percent aq. CHCl₂CO₂H / 0.5 h / 0 °C

2: 1) mesyl chloride, 2) LiAlH₄ / 1) pyridine, 0 deg C, 1 h, 2) Et₂O, r.t., 2 h

3: 96 percent / 1) Ac₂O, concd. H₂SO₄, 2) 1 M aq. NaOH / 1) 0 deg C, 10 min, 2) r.t., 3.5 h

4: 86 percent / diethyl ether / 20 h / 35 °C

5: 1) concd. H₂SO₄, dimethoxypropane, 2) DMAP / 1) 0 deg C, 0.5 h, 2) EtOAc, r.t., 0.5 h

With dichloro-acetic acid; dmap; sodium hydroxide; lithium aluminium tetrahydride; dimethoxypropane; sulfuric acid; acetic anhydride; methanesulfonyl chloride; In diethyl ether;

DOI:10.1246/bcsj.58.3457

upstream raw materials:

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside

benzyl bromide

Downstream raw materials:

methyl 2-O-benzyl-3-deoxy-3-C-methyl-α-D-altropyranoside

methyl 2-O-benzyl-3,6-dideoxy-3-C-methyl-α-D-altropyranoside