methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside
• CAS No.: 126456-16-4
• Molecular Formula: C₁₆H₁₆F₆O₁₀S₂
• Molecular Weight: 546.419
• Mol file: 126456-16-4.mol

Synonyms:methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside

Chemical Property of methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside

There total 5 articles about methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-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: 85.0%

trifluoromethylsulfonic anhydride (358-23-6) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → 4,6-O-benzylidene-1-O-methyl-2-O-trifluoromethylsulfonate-α-D-glucopyranoside (129217-24-9) + methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside (126456-16-4)

Guidance literature:

With pyridine; In dichloromethane; at -20 ℃; for 2h;

DOI:10.1021/jo00309a013

Reference yield: 80.0%

trifluoromethylsulfonic anhydride (358-23-6) + 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside (3162-96-7) → methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside (126456-16-4)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1055/s-0036-1588624

Reference yield:

methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside (126456-16-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / camphor sulfonic acid / dimethylformamide / 60 °C / 180.01 Torr

2: pyridine / CH₂Cl₂ / 3 h / -30 °C

With pyridine; camphor-10-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(03)00288-X

upstream raw materials:

trifluoromethylsulfonic anhydride

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

benzaldehyde dimethyl acetal

methyl-alpha-D-glucopyranoside

Downstream raw materials:

(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose