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

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-thiopyran-3-yl ester
• CAS No.: 146609-14-5
• Molecular Formula: C₃₅H₄₂O₁₄S
• Molecular Weight: 718.776

Synonyms:Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-thiopyran-3-yl ester

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

Chemical Property:

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

There total 3 articles about Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-thiopyran-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: 70.0%

methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside (76419-48-2) + 2,3,4,6-tetra-O-acetyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate (146558-06-7) → 3,4,6-tri-O-acetyl-1,2-(methyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranos-2-yl)-α-D-5'-thio-α-D-glucopyranose orthoacetate (146558-08-9) + methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2,3,4,6-tetra-O-acetyl-5'-thio-α-D-glucopyranosyl)-α-D-glucopyranoside (146558-07-8) + Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-thiopyran-3-yl ester (146609-14-5)

Guidance literature:

With 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -78 ℃; for 3.5h;

DOI:10.1016/0040-4039(93)88013-9

Reference yield:

1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose (10470-80-1) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-thiopyran-3-yl ester (146609-14-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / hydrazine acetate / dimethylformamide / 3 h

2: 81 percent / potassium carbonate / CH₂Cl₂ / 24 h

3: 23 percent / triethylsilyl triflate, 4 A molecular sieves / CH₂Cl₂ / 6.5 h / -78 °C

With 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0957-4166(00)80386-9

Reference yield:

2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose (137886-82-9) → Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,4aR,6S,7R,8S,8aR)-8-benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-tetrahydro-thiopyran-3-yl ester (146609-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / potassium carbonate / CH₂Cl₂ / 24 h

2: 23 percent / triethylsilyl triflate, 4 A molecular sieves / CH₂Cl₂ / 6.5 h / -78 °C

With 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; potassium carbonate; In dichloromethane;

DOI:10.1016/S0957-4166(00)80386-9

upstream raw materials:

methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose

2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose

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