Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3S,4R,6R)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3S,4R,6R)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 111462-48-7
• Molecular Formula: C₄₄H₅₄O₁₅Si
• Molecular Weight: 850.989

Synonyms:

Chemical Property of Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3S,4R,6R)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3S,4R,6R)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3S,4R,6R)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 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:

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (111462-47-6) → Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3S,4R,6R)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (111462-48-7)

Guidance literature:

With molecular sives 3A; pyridinium chlorochromate; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(87)84003-X

Reference yield:

methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (78077-24-4) → Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3S,4R,6R)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (111462-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / imidazole / dimethylformamide / 1 h / 0 °C

2: 4 g / pyridinium chlorochromate, molecular sives 3A / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; molecular sives 3A; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(87)84003-X

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2S,3S,4R,6R)-4-benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester (111462-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / imidazole / dimethylformamide / 1 h / 0 °C

2: 4 g / pyridinium chlorochromate, molecular sives 3A / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; molecular sives 3A; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(87)84003-X

upstream raw materials:

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

methyl 3-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

tert-butylchlorodiphenylsilane

Downstream raw materials:

methyl 3-O-benzyl-2-O-α-D-mannopyranosyl-α-D-talopyranoside

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-talopyranoside

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-α-D-mannopyranosyl-α-D-talopyranoside

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