Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(formyl)-α-D-galactopyranoside

Base Information

• Chemical Name: Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(formyl)-α-D-galactopyranoside
• CAS No.: 139070-99-8
• Molecular Formula: C₂₉H₃₂O₆
• Molecular Weight: 476.569
• Mol file: 139070-99-8.mol

Synonyms:Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(formyl)-α-D-galactopyranoside

Chemical Property of Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(formyl)-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(formyl)-α-D-galactopyranoside

There total 11 articles about Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(formyl)-α-D-galactopyranoside 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%

((2S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-methanol (127243-54-3,127924-50-9) → (2S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-carbaldehyde (127214-51-1,139070-99-8)

Guidance literature:

With triethylamine; In dichloromethane; dimethyl sulfoxide; -78 to -48 deg C;

DOI:10.1016/S0040-4039(00)76178-8

Reference yield:

alpha-D-glucopyranose (492-62-6) → (2S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-carbaldehyde (127214-51-1,139070-99-8)

Guidance literature:

Multi-step reaction with 3 steps

2: 2.) thexylborane, H₂O₂, NaOH / 1.) THF, o deg C to room temp.; 2.) THF

3: 98 percent / ClCOCOC, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 to -48 deg C

With sodium hydroxide; thexylborane; dihydrogen peroxide; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)76178-8

Reference yield:

benzyl bromide (100-39-0) → (2S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-carbaldehyde (127214-51-1,139070-99-8)

Guidance literature:

Multi-step reaction with 3 steps

2: 2.) thexylborane, H₂O₂, NaOH / 1.) THF, o deg C to room temp.; 2.) THF

3: 98 percent / ClCOCOC, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 to -48 deg C

With sodium hydroxide; thexylborane; dihydrogen peroxide; triethylamine; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)76178-8

upstream raw materials:

((2S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-methanol

alpha-D-glucopyranose

benzyl bromide

(2R,4R,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-dihydro-pyran-3-one

Downstream raw materials:

methyl 2,3,6-Tri-O-Benzyl-4-Deoxy-4-Formyl-α-D-Gluco-Pyranoside

methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside

METHYL 2,3,6-TRI-O-BENZYL-4-DEOXY-4-HYDROXYMETHYL-α-D-GLUCO-PYRANOSIDE

Methyl 4-C-(6-O-Acetyl-3,4,5,7-tetra-O-benzyl-2-heptulo-D-glucos-1-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside