methyl 3-chloro-4,6-O-cyclohexylidene-2,3-dideoxy-2-p-toluenesulfonamido-β-D-allopyranoside

Base Information

• Chemical Name: methyl 3-chloro-4,6-O-cyclohexylidene-2,3-dideoxy-2-p-toluenesulfonamido-β-D-allopyranoside
• CAS No.: 78138-81-5
• Molecular Formula: C₂₀H₂₈ClNO₆S
• Molecular Weight: 445.964
• Mol file: 78138-81-5.mol

Synonyms:methyl 3-chloro-4,6-O-cyclohexylidene-2,3-dideoxy-2-p-toluenesulfonamido-β-D-allopyranoside

Chemical Property of methyl 3-chloro-4,6-O-cyclohexylidene-2,3-dideoxy-2-p-toluenesulfonamido-β-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-chloro-4,6-O-cyclohexylidene-2,3-dideoxy-2-p-toluenesulfonamido-β-D-allopyranoside

There total 4 articles about methyl 3-chloro-4,6-O-cyclohexylidene-2,3-dideoxy-2-p-toluenesulfonamido-β-D-allopyranoside 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: 71.0%

methyl 2-deoxy-3-O-tolylsulfonyl-2-p-toluenesulfonamido-β-D-glucopyranoside (78138-80-4) → methyl 3-chloro-4,6-O-cyclohexylidene-2,3-dideoxy-2-p-toluenesulfonamido-β-D-allopyranoside (78138-81-5)

Guidance literature:

With lithium chloride; In N,N-dimethyl-formamide; at 120 ℃; for 1h;

DOI:10.1016/S0008-6215(00)85251-9

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(p-toluenesulfonyl)amido-α-D-glucopyranose (63301-57-5) → methyl 3-chloro-4,6-O-cyclohexylidene-2,3-dideoxy-2-p-toluenesulfonamido-β-D-allopyranoside (78138-81-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 4.94 g / HBr / CH₂Cl₂ / 0 °C

2: 1.) pyridine; 2.) 0.5 M NaOMe / 1.) 20 min, RT, 17 h, RT; 2.) 2 h, RT, methanol

3: 93 percent / p-toluenesulfonic acid / dimethylformamide / 1.5 h / 50 °C / 15 Torr

4: 67 percent / pyridine / 16 h / 90 °C

5: 71 percent / anhydrous LiCl / dimethylformamide / 1 h / 120 °C

With pyridine; hydrogen bromide; sodium methylate; toluene-4-sulfonic acid; lithium chloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)85251-9

Reference yield:

methyl 4,6-O-cyclohexylidene-2-deoxy-2-p-toluenesulfonamido-β-D-glucopyranoside (78138-79-1) → methyl 3-chloro-4,6-O-cyclohexylidene-2,3-dideoxy-2-p-toluenesulfonamido-β-D-allopyranoside (78138-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / pyridine / 16 h / 90 °C

2: 71 percent / anhydrous LiCl / dimethylformamide / 1 h / 120 °C

With pyridine; lithium chloride; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)85251-9

upstream raw materials:

methyl 2-deoxy-3-O-tolylsulfonyl-2-p-toluenesulfonamido-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(p-toluenesulfonyl)amido-α-D-glucopyranose

methyl 4,6-O-cyclohexylidene-2-deoxy-2-p-toluenesulfonamido-β-D-glucopyranoside

methyl 2-deoxy-2-p-toluenesulfonamido-β-D-glucopyranoside