methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate

Base Information

• Chemical Name: methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate
• CAS No.: 450409-36-6
• Molecular Formula: C₃₇H₃₆O₉
• Molecular Weight: 624.687
• Mol file: 450409-36-6.mol

Synonyms:methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate

Chemical Property of methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate

There total 1 articles about methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate 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: 70.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + methyl (methyl 4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-2-octulopyranosid)onate (93215-23-7) → methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate (450409-36-6)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1007/s007060200029

Reference yield: 84.0%

methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate (450409-36-6) → methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)-onate (450409-37-7)

Guidance literature:

With formic acid; In diethyl ether; acetonitrile; for 17h;

DOI:10.1007/s007060200029

Reference yield:

methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate (450409-36-6) → methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-(S)-[8-2H]-α-D-manno-oct-2-ulopyranosid)-onate

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / formic acid / acetonitrile; diethyl ether / 17 h

2: 87 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.25 h / -40 °C

3: N-benzyloxycarbonyl-(S)-proline; NaBD₄ / D₂O; tetrahydrofuran / 0.5 h / -126 °C

With formic acid; sodium borodeuteride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-Benzyloxycarbonyl-L-proline; In tetrahydrofuran; diethyl ether; dichloromethane; water-d2; acetonitrile; 2: Swern oxidation;

DOI:10.1007/s007060200029

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

methyl (methyl 4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-2-octulopyranosid)onate

Downstream raw materials:

methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)-onate

methyl (methyl 2-O-benzyl-4,5-O-carbonyl-6-deoxy-α-D-manno-oct-7-ulo-4,7-pyranosid)-onate