methyl 3-O-(3-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside

Base Information

• Chemical Name: methyl 3-O-(3-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside
• CAS No.: 129110-26-5
• Molecular Formula: C₃₆H₄₂O₁₀
• Molecular Weight: 634.723

Synonyms:methyl 3-O-(3-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside

Chemical Property of methyl 3-O-(3-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-(3-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside

There total 7 articles about methyl 3-O-(3-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-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:

benzaldehyde dimethyl acetal (1125-88-8) → methyl 3-O-(3-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside (129110-26-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / (+/-)-camphor-10-sulfonic acid / dimethylformamide / 3 h / 80 °C / 52.5 Torr

2: 89 percent / pyridinium chlorochromate, molecular sieves (4 Angstroem) / CH₂Cl₂ / 2 h / Ambient temperature

3: 2. LiAlH₄ / 1. 95percent aq. EtOH, room temperature 2. THF, room temperature, 15 min

4: 1. KH / 1. THF, 1 h, room temperature 2. 90 min

With lithium aluminium tetrahydride; 4 A molecular sieve; camphor-10-sulfonic acid; potassium hydride; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84084-8

Reference yield:

methyl 2-O-benzyl-6-deoxy-3-O-(2-deoxy-β-D-arabino-hexopyranosyl)-4-O-methyl-β-D-galactopyranoside (129081-07-8) → methyl 3-O-(3-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside (129110-26-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / (+/-)-camphor-10-sulfonic acid / dimethylformamide / 3 h / 80 °C / 52.5 Torr

2: 89 percent / pyridinium chlorochromate, molecular sieves (4 Angstroem) / CH₂Cl₂ / 2 h / Ambient temperature

3: 2. LiAlH₄ / 1. 95percent aq. EtOH, room temperature 2. THF, room temperature, 15 min

4: 1. KH / 1. THF, 1 h, room temperature 2. 90 min

With lithium aluminium tetrahydride; 4 A molecular sieve; camphor-10-sulfonic acid; potassium hydride; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84084-8

Reference yield:

methyl 2-O-benzyl-6-deoxy-4-O-methyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-β-D-arabino-hexapyranosyl)-β-D-galactopyranoside (125084-98-2) → methyl 3-O-(3-O-benzoyl-4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside (129110-26-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / NaOCH₃ / methanol / 1.5 h / Ambient temperature

2: 96 percent / (+/-)-camphor-10-sulfonic acid / dimethylformamide / 3 h / 80 °C / 52.5 Torr

3: 89 percent / pyridinium chlorochromate, molecular sieves (4 Angstroem) / CH₂Cl₂ / 2 h / Ambient temperature

4: 2. LiAlH₄ / 1. 95percent aq. EtOH, room temperature 2. THF, room temperature, 15 min

5: 1. KH / 1. THF, 1 h, room temperature 2. 90 min

With lithium aluminium tetrahydride; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; potassium hydride; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(90)84084-8

upstream raw materials:

methyl 2-O-benzyl-3-O-(4,6-O-benzylidene-2-deoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-6-deoxy-4-O-methyl-β-D-galactopyranoside

benzoyl chloride

benzaldehyde dimethyl acetal

methyl 2-O-benzyl-6-deoxy-3-O-(2-deoxy-β-D-arabino-hexopyranosyl)-4-O-methyl-β-D-galactopyranoside

Downstream raw materials:

methyl O-<3,4-di-O-benzyl-2,6-dideoxy-1(R)-D-arabino-hexopyranosylidene>-(1->3,4)-O-(2,6-dideoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-(1->3)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside

(2R,3R,4R,6S)-6-((2R,3R,4S,5S,6R)-3-Benzyloxy-2,5-dimethoxy-6-methyl-tetrahydro-pyran-4-yloxy)-3-((2R,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-2-yloxy)-2,4-dimethyl-tetrahydro-pyran-4-ol

C₄₈H₆₀O₁₂Se

methyl O-(3,4-di-O-benzyl-2,6-dideoxy-2-phenylseleno-α-D-mannopyranosyl)-(1->4)-O-(3-O-benzoyl-2,6-dideoxy-3-C-methyl-β-D-arabino-hexopyranosyl)-(1->3)-2-O-benzyl-6-deoxy-4-O-methyl-β-D-galactopyranoside

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