methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentodialdo-1,4-furanoside

Base Information

• Chemical Name: methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentodialdo-1,4-furanoside
• CAS No.: 268203-17-4
• Molecular Formula: C₁₄H₁₈O₄
• Molecular Weight: 250.295
• Mol file: 268203-17-4.mol

Synonyms:

Chemical Property of methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentodialdo-1,4-furanoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentodialdo-1,4-furanoside

There total 9 articles about methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentodialdo-1,4-furanoside 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:

methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentofuranoside (268203-16-3) → methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentodialdo-1,4-furanoside (268203-17-4)

Guidance literature:

With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; at -78 - 20 ℃; for 1h;

DOI:10.1016/S0957-4166(99)00563-7

Reference yield:

methyl 2-deoxy-5-O-trityl-β-D-glycero-pentofuranosid-3-ulose (51921-34-7) → methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentodialdo-1,4-furanoside (268203-17-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C

2: 87 percent / KOH / 2 h / 130 - 140 °C

3: Amberlyst-15 macroreticular resin (strongly acidic) / methanol / 8 h / 20 °C

4: 0.6 g / DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

With potassium hydroxide; cerium(III) chloride; Amberlyst-15 macroreticular resin (strongly acidic); dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Methylation / 2: benzylation / 3: detritylation / 4: Oxidation;

DOI:10.1016/S0957-4166(99)00563-7

Reference yield:

methyl 2-deoxy-5-O-trityl-α-D-glycero-pentofuranosid-3-ulose (51885-24-6) → methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentodialdo-1,4-furanoside (268203-17-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / CeCl₃ / tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C

2: 70 percent / KOH / 2 h / 130 - 140 °C

3: Amberlyst-15 macroreticular resin (strongly acidic) / methanol / 8 h / 20 °C

4: 0.6 g / DMSO; trifluoroacetic anhydride; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

With potassium hydroxide; cerium(III) chloride; Amberlyst-15 macroreticular resin (strongly acidic); dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Methylation / 2: benzylation / 3: detritylation / 4: Oxidation;

DOI:10.1016/S0957-4166(99)00563-7

upstream raw materials:

methyl 3-O-benzyl-2-deoxy-3-C-methyl-β-D-threo-pentofuranoside

methyl 2-deoxy-5-O-trityl-α-D-glycero-pentofuranosid-3-ulose

methyl 2-deoxy-5-O-trityl-β-D-glycero-pentofuranosid-3-ulose

methyl 2-deoxy-5-O-trityl-α-D-erythro-pentofuranoside