methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside

Base Information

• Chemical Name: methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside
• CAS No.: 497234-45-4
• Molecular Formula: C₁₉H₂₉O₈P
• Molecular Weight: 416.408
• Mol file: 497234-45-4.mol

Synonyms:methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside

Chemical Property of methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside

There total 11 articles about methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside 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%

Oxalic acid 2-benzyloxy-1-(dimethoxy-phosphoryl)-1-((3aR,4S,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester methyl ester → methyl (5S)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-β-L-gulofuranoside (497234-46-5) + methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside (497234-45-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃;

DOI:10.1016/S0008-6215(03)00235-0

Reference yield: 16.0%

Oxalic acid (R)-2-benzyloxy-1-(dimethoxy-phosphoryl)-1-((3aR,4S,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester methyl ester → methyl (5S)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-β-L-gulofuranoside (497234-46-5) + methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside (497234-45-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 2h;

DOI:10.1002/1522-2675(200209)85:9<2608::AID-HLCA2608>3.0.CO;2-F

Reference yield: 15.0%

Oxalic acid (S)-2-benzyloxy-1-(dimethoxy-phosphoryl)-1-((3aR,4S,6S,6aS)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester methyl ester → methyl (5S)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-β-L-gulofuranoside (497234-46-5) + methyl (5R)-6-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-2,3-O-isopropylidene-α-D-mannofuranoside (497234-45-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 80 ℃; for 2h;

DOI:10.1002/1522-2675(200209)85:9<2608::AID-HLCA2608>3.0.CO;2-F

upstream raw materials:

methyl 2,3-O-isopropylidene-α-D-mannofuranoside

methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannofuranoside

methyl 6-O-benzyl-2,3-O-isopropylidene-α-D-mannofuranoside

methyl 5,6-anhydro-2,3-O-isopropylidene-α-D-mannofuranoside