Methyl 3-O-allyl-2-O-benzyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl 3-O-allyl-2-O-benzyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside
• CAS No.: 142967-65-5
• Molecular Formula: C₂₄H₃₀O₈S
• Molecular Weight: 478.563
• Mol file: 142967-65-5.mol

Synonyms:Methyl 3-O-allyl-2-O-benzyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside

Chemical Property of Methyl 3-O-allyl-2-O-benzyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 3-O-allyl-2-O-benzyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside

There total 5 articles about Methyl 3-O-allyl-2-O-benzyl-6-O-p-tolylsulfonyl-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: 91.0%

Methyl 3-O-allyl-2-O-benzyl-α-D-glucopyranoside (58341-57-4) + p-toluenesulfonyl chloride (98-59-9) → Methyl 3-O-allyl-2-O-benzyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside (142967-65-5)

Guidance literature:

With pyridine;

DOI:10.1016/S0008-6215(00)90481-6

Reference yield:

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) → Methyl 3-O-allyl-2-O-benzyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside (142967-65-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH; TBAI / tetrahydrofuran; various solvent(s) / 24 h

2: TsOH / methanol

3: pyridine / 0 - 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol;

DOI:10.1021/ol027288c

Reference yield:

methyl 2-O-benzyl-3-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside (203717-51-5) → Methyl 3-O-allyl-2-O-benzyl-6-O-p-tolylsulfonyl-α-D-glucopyranoside (142967-65-5)

Guidance literature:

Multi-step reaction with 2 steps

1: TsOH / methanol

2: pyridine / 0 - 20 °C

With toluene-4-sulfonic acid; In pyridine; methanol;

DOI:10.1021/ol027288c

upstream raw materials:

Methyl 3-O-allyl-2-O-benzyl-α-D-glucopyranoside

p-toluenesulfonyl chloride

methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

methyl 2-O-benzyl-3-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

methyl 3-O-allyl-2-O-benzyl-6-deoxy-α-D-glucopyranoside

methyl 3-O-allyl-2-O-benzyl-6-deoxy-α-D-galactopyranoside

methyl 3-O-allyl-4-azido-2-O-benzyl-4,6-dideoxy-α-D-glucopyranoside

methyl 3-O-(2-hydroxyethyl)-4-azido-2-O-benzyl-4,6-dideoxy-α-D-glucopyranoside