3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose

Base Information

• Chemical Name: 3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose
• CAS No.: 10227-17-5
• Molecular Formula: C₁₅H₂₂O₈S
• Molecular Weight: 362.401
• DSSTox Substance ID: DTXSID60452809
• Mol file: 10227-17-5.mol

Synonyms:10227-17-5;3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose;[2-[(3aR,5S,6R,6aR)-6-acetyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-acetylsulfanylethyl] acetate;3,6-Di-O-acetyl-5-S-acetyl-5-deoxy-1,2-O-isopropylidene-a-D-glucofuranose;DTXSID60452809;GCYIJZBDQYYVLT-ZLMOABSSSA-N;W-200663

Chemical Property of 3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose

Chemical Property:

• PSA: 122.66000
• LogP: 1.00590
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 362.10353883
• Heavy Atom Count: 24
• Complexity: 520

Purity/Quality:

98%,99%, ^*data from raw suppliers

3,6-Di-O-acetyl-5-S-acetyl-5-deoxy-1,2-O-isopropylidene-a-D-glucofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(C1C(C2C(O1)OC(O2)(C)C)OC(=O)C)SC(=O)C
• Isomeric SMILES: CC(=O)OCC([C@@H]1[C@@H]([C@@H]2[C@H](O1)OC(O2)(C)C)OC(=O)C)SC(=O)C

Technology Process of 3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose

There total 7 articles about 3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose 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: 98.0%

5,6-anhydro-5,6-epithio-1,2-O-isopropylidene-α-D-glucofuranose (37614-79-2) + acetic anhydride (108-24-7) → 3,6-di-O-acetyl-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose (10227-17-5)

Guidance literature:

With sodium acetate; In acetic acid; for 5h; Heating;

Reference yield: 91.0%

acetic anhydride (108-24-7) + Acetic acid (R)-2-acetylsulfanyl-2-((3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester → 3,6-di-O-acetyl-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose (10227-17-5)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1081/SCC-120014042

Reference yield:

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (16713-80-7) → 3,6-di-O-acetyl-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose (10227-17-5)

Guidance literature:

Multi-step reaction with 3 steps

2: 66 percent / 0.05M NaOMe / methanol / 9 h / Ambient temperature

3: 1.) thiourea, 2.) KOAc / 1.) MeOH, RT, 5d, 2.) AcOH, 140 deg C, 19h

With sodium methylate; potassium acetate; thiourea; In methanol;

upstream raw materials:

5,6-anhydro-5,6-epithio-1,2-O-isopropylidene-α-D-glucofuranose

acetic anhydride

5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

(3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetraol

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

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

methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside