(3aS,4S,6R,7aR)-4-[(2S,3S,4R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one

Base Information

• Chemical Name: (3aS,4S,6R,7aR)-4-[(2S,3S,4R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one
• CAS No.: 111462-56-7
• Molecular Formula: C₅₅H₆₆O₁₁Si₂
• Molecular Weight: 959.293

Synonyms:

Chemical Property of (3aS,4S,6R,7aR)-4-[(2S,3S,4R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3aS,4S,6R,7aR)-4-[(2S,3S,4R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one

There total 4 articles about (3aS,4S,6R,7aR)-4-[(2S,3S,4R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one 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-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside (111462-55-6) → (3aS,4S,6R,7aR)-4-[(2S,3S,4R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one (111462-56-7)

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) → (3aS,4S,6R,7aR)-4-[(2S,3S,4R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one (111462-56-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / 0.1 M sodium methoxide / methanol / 4 h / Ambient temperature

2: 81 percent / imidazol / dimethylformamide / 1 h / 0 °C

3: 89 percent / p-toluenesulfonic acid monohydrate / acetone / 1 h / Ambient temperature

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

With 1H-imidazole; molecular sives 3A; sodium methylate; toluene-4-sulfonic acid; pyridinium chlorochromate; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

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

Reference yield:

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside (111462-54-5) → (3aS,4S,6R,7aR)-4-[(2S,3S,4R,6R)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxy-5-oxo-tetrahydro-pyran-3-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one (111462-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / p-toluenesulfonic acid monohydrate / acetone / 1 h / Ambient temperature

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

With molecular sives 3A; toluene-4-sulfonic acid; pyridinium chlorochromate; In dichloromethane; acetone;

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

upstream raw materials:

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(2,3-O-isopropylidene-6-O-tert-butyldiphenylsilyl-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

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-α-D-mannopyranosyl)-α-D-mannopyranoside

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

Downstream raw materials:

(2R,3S,4S,5R,6R)-2-((2S,3S,4S,5S,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

methyl 3-O-benzyl-2-O-(2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

methyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-O-(6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-talopyranosyl)-α-D-talopyranoside

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