methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-nitro-3-C-tolylsulfonyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-nitro-3-C-tolylsulfonyl-α-D-glucopyranoside
• CAS No.: 116113-87-2
• Molecular Formula: C₂₁H₂₃NO₈S
• Molecular Weight: 449.482

Synonyms:methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-nitro-3-C-tolylsulfonyl-α-D-glucopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-nitro-3-C-tolylsulfonyl-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-nitro-3-C-tolylsulfonyl-α-D-glucopyranoside

There total 2 articles about methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-nitro-3-C-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: 94.0%

p-toluenesulfinic acid sodium salt dihydrate (824-79-3,7257-26-3) + methyl 4,6-O-benzylidene-2,3-dideoxy-2-nitro-α-D-erythro-hex-2-enopyranoside (74511-16-3) → methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-nitro-3-C-tolylsulfonyl-α-D-glucopyranoside (116113-87-2)

Guidance literature:

cetyltributylphosphonium bromide; In water; acetic acid; benzene; for 6h; Ambient temperature;

DOI:10.1016/0008-6215(87)80250-1

Reference yield:

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-2-C-p-tolylsulfonyl-α-D-mannopyranoside (111614-25-6) → methyl 4,6-O-benzylidene-2,3-dideoxy-2-nitro-α-D-erythro-hex-2-enopyranoside (74511-16-3) + methyl 4,6-O-benzylidene-2-deoxy-2-nitro-α-D-glucopyranoside (79528-58-8) + methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-nitro-3-C-tolylsulfonyl-α-D-glucopyranoside (116113-87-2) + methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-p-tolylsulfonyl-α-D-erythro-hex-2-enopyranoside (111549-50-9)

Guidance literature:

With triethylamine; In dichloromethane; for 1h; Yield given. Further byproducts given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/0008-6215(87)80250-1

Reference yield:

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-nitro-3-C-tolylsulfonyl-α-D-glucopyranoside (116113-87-2) → methyl 4,6-O-benzylidene-2,3-dideoxy-2-nitro-α-D-erythro-hex-2-enopyranoside (74511-16-3) + methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-C-p-toluenesulfonyl-α-D-erythro-hex-2-enopyranoside (116113-86-1)

Guidance literature:

With triethylamine; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1016/0008-6215(87)80250-1

upstream raw materials:

p-toluenesulfinic acid sodium salt dihydrate

methyl 4,6-O-benzylidene-2,3-dideoxy-2-nitro-α-D-erythro-hex-2-enopyranoside

methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-nitro-2-C-p-tolylsulfonyl-α-D-mannopyranoside

Downstream raw materials:

methyl 4,6-O-benzylidene-2,3-dideoxy-2-nitro-α-D-erythro-hex-2-enopyranoside

methyl 2,3-dideoxy-4,6-O-(phenylmethylene)-3-C-p-toluenesulfonyl-α-D-erythro-hex-2-enopyranoside

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