beta-D-Glucopyranoside, 2-propenyl 2-(acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-

Base Information

• Chemical Name: beta-D-Glucopyranoside, 2-propenyl 2-(acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-
• CAS No.: 65947-37-7
• Molecular Formula: C18H23NO6
• Molecular Weight: 349.384
• Mol file: 65947-37-7.mol

Synonyms:.beta.-D-Glucopyranoside, 2-propenyl 2-(acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-;Allyl 2-(Acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-alpha-D-glucopyranoside;SCHEMBL21394611

Chemical Property of beta-D-Glucopyranoside, 2-propenyl 2-(acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 599.33°C at 760 mmHg
• Flash Point: 316.264°C
• PSA: 86.25000
• Density: 1.272g/cm³
• LogP: 1.28460
• Solubility.: Methanol
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 349.15253745
• Heavy Atom Count: 25
• Complexity: 467

Purity/Quality:

99% ^*data from raw suppliers

Allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C2C(COC(O2)C3=CC=CC=C3)OC1OCC=C)O

Technology Process of beta-D-Glucopyranoside, 2-propenyl 2-(acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-

There total 19 articles about beta-D-Glucopyranoside, 2-propenyl 2-(acetylamino)-2-deoxy-4,6-O-(phenylmethylene)- 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: 100.0%

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside (54400-75-8,64650-83-5,88903-97-3,116347-86-5,140849-88-3,144300-01-6,54400-77-0) + benzaldehyde dimethyl acetal (1125-88-8) → allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (63064-49-3,65947-37-7,74984-84-2,88903-98-4,92841-84-4,116347-88-7,136845-44-8,138456-61-8,74984-83-1)

Guidance literature:

With camphor-10-sulfonic acid; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1002/cbic.201700251

Reference yield: 93.0%

allyl 2-acetamido-3-O-acetyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (508194-14-7) → allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside (63064-49-3,65947-37-7,74984-84-2,88903-98-4,92841-84-4,116347-88-7,136845-44-8,138456-61-8,74984-83-1)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/0008-6215(90)84083-7

Reference yield: 85.0%

benzaldehyde dimethyl acetal (1125-88-8) → allyl 2-deoxy-2-acetamido-4,6-O-benzylidene-β-D-glucopyranoside (65947-37-7)

Guidance literature:

allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside; With methanol; sodium methylate;

benzaldehyde dimethyl acetal; With (1S)-10-camphorsulfonic acid; In N,N-dimethyl-formamide;

upstream raw materials:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside

benzaldehyde dimethyl acetal

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

Downstream raw materials:

allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside

N-{(4aR,6R,7R,8R,8aS)-8-Benzyloxy-2-phenyl-6-[((E)-propenyl)oxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

allyl 2-acetamido-4,6-O-benzylidene-3-O-(2-butenyl)-2-deoxy-β-D-glucopyranoside

allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside