methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside

Base Information

• Chemical Name: methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside
• CAS No.: 74857-70-8
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Mol file: 74857-70-8.mol

Synonyms:methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside

Chemical Property of methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside

There total 3 articles about methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside 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: 86.0%

benzoyl chloride (98-88-4) + methyl 3-azido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside (74857-68-4) → methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside (74857-70-8)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1021/ja00531a050

Reference yield: 83.0%

benzoyl chloride (98-88-4) + methyl 3-amino-3,4-dideoxy-4-C-methylene-α-L-threo-pentapyranoside (92539-74-7) → methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside (74857-70-8)

Guidance literature:

With sodium hydrogencarbonate; In chloroform; for 1h; Ambient temperature;

DOI:10.1139/v84-261

Reference yield:

methyl 2,3-anhydro-4-C-methylene-β-D-erythro-pentopyranoside (74872-27-8) → methyl 3-benzamido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside (74857-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) ammonia / 1.) ethanol, ice bath; 2.) 80 deg C, 30 min

2: 83 percent / sodium bicarbonate / CHCl₃ / 1 h / Ambient temperature

With ammonia; sodium hydrogencarbonate; In chloroform;

DOI:10.1139/v84-261

upstream raw materials:

benzoyl chloride

methyl 3-azido-3,4-dideoxy-4-C-methylene-α-L-threo-pentopyranoside

methyl 3-amino-3,4-dideoxy-4-C-methylene-α-L-threo-pentapyranoside

methyl 2,3-anhydro-4-C-methylene-β-D-erythro-pentopyranoside

Downstream raw materials:

(3aR,6R,7R,7aR)-3a-Iodomethyl-6-methoxy-2-phenyl-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]oxazol-7-ol

2'-phenyl-(methyl 3,4-dideoxy-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

2'-phenyl-(methyl 3,4-dideoxy-2-O-α-ethoxyethyl-4-C-iodomethyl-α-L-arabinopyranosido)-<3,4:4',5'>-Δ^2'-oxazoline

methyl 3-benzamido-3,4-dideoxy-2-O-α-ethoxyethyl-4-C-methylene-α-L-threo-pentopyranoside