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

Base Information

Chemical Name:(2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-thiopyran-3,4,5-triol
CAS No.:1053624-48-8
Molecular Formula:C₂₀H₃₀O₁₀S
Molecular Weight:462.518
Hs Code.:

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

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

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

There total 6 articles about (2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-thiopyran-3,4,5-triol 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:

: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2S,3R,4S,5R,6R)-4-benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-thiopyran-3-yl ester

: 1053624-48-8
(2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-thiopyran-3,4,5-triol

Guidance literature:: With ammonia; In methanol;
DOI:10.1016/S0957-4166(00)80386-9

Reference yield:

: 10470-80-1
1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose

: 1053624-48-8
(2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-thiopyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: 68 percent / triethylsilyl triflate, 4 A molecular sieves / CH₂Cl₂ / 6.5 h / -78 °C

4: 80percent aq. acetic acid / 4 h / 50 °C

5: ammonia / methanol

With 4 A molecular sieve; ammonia; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; potassium carbonate; acetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(00)80386-9

Reference yield:

: 137886-82-9
2,3,4,6-tetra-O-acetyl-5-thio-D-glucopyranose

: 1053624-48-8
(2S,3R,4S,5S,6R)-2-((2S,3R,4S,5R,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-thiopyran-3,4,5-triol

Guidance literature:: Multi-step reaction with 4 steps

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

2: 68 percent / triethylsilyl triflate, 4 A molecular sieves / CH₂Cl₂ / 6.5 h / -78 °C

3: 80percent aq. acetic acid / 4 h / 50 °C

4: ammonia / methanol

With 4 A molecular sieve; ammonia; triethylsilyl trifluoromethyl sulfonate; potassium carbonate; acetic acid; In methanol; dichloromethane;
DOI:10.1016/S0957-4166(00)80386-9