S,S-dioxo-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol

Base Information

• Chemical Name: S,S-dioxo-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol
• CAS No.: 252851-36-8
• Molecular Formula: C₇₀H₇₄O₁₂S
• Molecular Weight: 1139.42
• Mol file: 252851-36-8.mol

Synonyms:S,S-dioxo-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol

Chemical Property of S,S-dioxo-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S,S-dioxo-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol

There total 5 articles about S,S-dioxo-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol 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: 79.0%

3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol (252851-47-1) → S,S-dioxo-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol (252851-36-8)

Guidance literature:

With Oxone; In tetrahydrofuran; methanol; water; at 60 ℃; for 3.5h;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → S,S-dioxo-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol (252851-36-8)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / tetrahydrofuran

2: LiAlH₄ / tetrahydrofuran

3: 86 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

4: 94 percent / K₂CO₃ / acetone / 36 h / Heating

5: 79 percent / Oxone^R / H₂O; methanol; tetrahydrofuran / 3.5 h / 60 °C

With Oxone; lithium aluminium tetrahydride; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

Reference yield:

ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate (82614-10-6) → S,S-dioxo-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol (252851-36-8)

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / tetrahydrofuran

2: 86 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

3: 94 percent / K₂CO₃ / acetone / 36 h / Heating

4: 79 percent / Oxone^R / H₂O; methanol; tetrahydrofuran / 3.5 h / 60 °C

With Oxone; lithium aluminium tetrahydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetone;

DOI:10.1002/1099-0690(200204)2002:7<1323::AID-EJOC1323>3.0.CO;2-8

upstream raw materials:

3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-S-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-2-deoxy-1thio-β-D-glycero-D-gulo-octitol

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol

ethyl 2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)acetate