methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate

Base Information

• Chemical Name: methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate
• CAS No.: 42400-52-2
• Molecular Formula: C₁₆H₁₈O₇
• Molecular Weight: 322.315
• Mol file: 42400-52-2.mol

Synonyms:methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate

Chemical Property of methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate

There total 8 articles about methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate 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: 98.0%

methyl 2-O-acetyl-4,6-O-benzylidene-α,D-glucopyranoside (25577-40-6) → methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate (42400-52-2)

Guidance literature:

With dipyridinium dichromate; 3 A molecular sieve; In dichloromethane; at 25 ℃; for 16h;

DOI:10.1021/ja00222a030

Reference yield:

(4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (4148-58-7) → methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate (42400-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluenesulfonic acid / CH₂Cl₂ / 30 h

2: 80percent acetic acid / H₂O / 0.33 h

3: dimethylsulfoxide, acetic anhydride / 20 h

With acetic anhydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; In dichloromethane; water;

DOI:10.1016/S0008-6215(00)80712-0

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate (42400-52-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 45 percent / p-toluenesulfonic acid / dimethylformamide

2: p-toluenesulfonic acid / CH₂Cl₂ / 30 h

3: 80percent acetic acid / H₂O / 0.33 h

4: dimethylsulfoxide, acetic anhydride / 20 h

With acetic anhydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)80712-0

upstream raw materials:

methyl 2-O-acetyl-4,6-O-benzylidene-α,D-glucopyranoside

methyl 2-O-acetyl-4,6-O-benzylidene-α-D-mannopyranoside

dimethyl sulfoxide

(4aR,6S,7S,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Downstream raw materials:

3-azido-4-O-(tert-butyldimethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate