methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside
• CAS No.: 128184-64-5
• Molecular Formula: C₂₉H₃₂O₅
• Molecular Weight: 460.57
• Mol file: 128184-64-5.mol

Synonyms:methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside

Chemical Property of methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside

There total 5 articles about methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside 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: 75.0%

methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside (138875-24-8) + Methylenetriphenylphosphorane (19493-09-5) → methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside (128184-64-5)

Guidance literature:

In benzene; at 25 ℃; for 0.25h;

DOI:10.1016/0008-6215(91)89017-A

Reference yield:

methyl 2,3,4-tri-O-benzyl-β-D-idopyranoside (128184-63-4,641635-63-4) → methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside (128184-64-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) oxalyl chloride, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2a) -78 deg C, 15 min, 2b) -78 to -40 deg C

2: 75 percent / benzene / 0.25 h / 25 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In benzene;

DOI:10.1016/0008-6215(91)89017-A

Reference yield:

(2R,3S,4R,5R)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran (128184-62-3) → methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-β-D-ido-hept-6-enopyranoside (128184-64-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) dicyclohexylborane, 2) 3M aq. NaOH, 30percent H₂O₂ / 1) THF, 25 deg C, 1.5h, 2) H₂O, 50 deg C, 20 min

2: 1) oxalyl chloride, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2a) -78 deg C, 15 min, 2b) -78 to -40 deg C

3: 75 percent / benzene / 0.25 h / 25 °C

With sodium hydroxide; oxalyl dichloride; bis(cyclohexanyl)borane; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In benzene;

DOI:10.1016/0008-6215(91)89017-A

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-b-D-ido-hexodialdo-1,5-pyranoside

Methylenetriphenylphosphorane

(2R,3S,4R,5R)-3,4,5-Tris-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran

methyl 2,3,4-tri-O-benzyl-β-D-idopyranoside

Downstream raw materials:

(2S,3R,4R,5R,6R)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanone

(1S,2R,3R,4R,5R,6S)-1,2,3-tribenzyloxy-6-methanesulfonyloxy-4-<(1-methylethyl)diethylsilyl>oxy-5-<<(1-methylethyl)diethylsilyl>oxy>methylcyclohexane

(1S,2R,3S,4R,5R,6S)-2,3,4-tribenzyloxy-5-<(1-methylethyl)diethylsilyl>oxy-6-<<(1-methylethyl)diethylsilyl>oxymethyl>cyclohexanol

(1R,2R,3S,4R,5R,6S)-2,3,4-Tris-benzyloxy-5-(diethyl-isopropyl-silanyloxy)-6-(diethyl-isopropyl-silanyloxymethyl)-cyclohexanol