Acetic acid (2R,4aR,6S,7S,8S,8aR)-8-methoxy-2-phenyl-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Base Information

• Chemical Name: Acetic acid (2R,4aR,6S,7S,8S,8aR)-8-methoxy-2-phenyl-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester
• CAS No.: 186540-08-9
• Molecular Formula: C₄₄H₅₀O₁₂
• Molecular Weight: 770.874

Synonyms:

Chemical Property of Acetic acid (2R,4aR,6S,7S,8S,8aR)-8-methoxy-2-phenyl-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,4aR,6S,7S,8S,8aR)-8-methoxy-2-phenyl-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

There total 6 articles about Acetic acid (2R,4aR,6S,7S,8S,8aR)-8-methoxy-2-phenyl-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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:

3-O-benzoyl-6-O-(t-butyldiphenyl)silyl-α-D-mannopyranoside (131089-34-4) → Acetic acid (2R,4aR,6S,7S,8S,8aR)-8-methoxy-2-phenyl-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (186540-08-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / Bu₄NI, NaH / tetrahydrofuran / 10 h / 25 °C

2: 93 percent / HF*pyridine / tetrahydrofuran / 16 h / 25 °C

3: 1.) N-iodosuccinamide, 2.) CF₃SO₃H / 1.) CH₂Cl₂, 25 deg C, 20 min, 2.) CH₂Cl₂, 0 deg C, 2 h

With N-Iodosuccinamide; trifluorormethanesulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridine hydrogenfluoride; In tetrahydrofuran;

DOI:10.1016/S0968-0896(96)00178-2

Reference yield:

tert-Butyl-diphenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane (186540-03-4) → Acetic acid (2R,4aR,6S,7S,8S,8aR)-8-methoxy-2-phenyl-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (186540-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / HF*pyridine / tetrahydrofuran / 16 h / 25 °C

2: 1.) N-iodosuccinamide, 2.) CF₃SO₃H / 1.) CH₂Cl₂, 25 deg C, 20 min, 2.) CH₂Cl₂, 0 deg C, 2 h

With N-Iodosuccinamide; trifluorormethanesulfonic acid; pyridine hydrogenfluoride; In tetrahydrofuran;

DOI:10.1016/S0968-0896(96)00178-2

Reference yield:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → Acetic acid (2R,4aR,6S,7S,8S,8aR)-8-methoxy-2-phenyl-6-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester (186540-08-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / imidazole / tetrahydrofuran / 4 h / 80 °C

2: 88 percent / Bu₄NI, NaH / tetrahydrofuran / 10 h / 25 °C

3: 93 percent / HF*pyridine / tetrahydrofuran / 16 h / 25 °C

4: 1.) N-iodosuccinamide, 2.) CF₃SO₃H / 1.) CH₂Cl₂, 25 deg C, 20 min, 2.) CH₂Cl₂, 0 deg C, 2 h

With 1H-imidazole; N-Iodosuccinamide; trifluorormethanesulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; pyridine hydrogenfluoride; In tetrahydrofuran;

DOI:10.1016/S0968-0896(96)00178-2

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

methyl 2-O-acetyl-3-O-methyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

3-O-benzoyl-6-O-(t-butyldiphenyl)silyl-α-D-mannopyranoside

methyl 1-thio-α-D-mannopyranoside

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