Ethyl 4,6-O-benzylidene-D-thiomannopyranoside

Base Information

• Chemical Name: Ethyl 4,6-O-benzylidene-D-thiomannopyranoside
• CAS No.: 142924-31-0
• Molecular Formula: C₁₅H₂₀O₅S
• Molecular Weight: 312.387
• DSSTox Substance ID: DTXSID701187070
• Mol file: 142924-31-0.mol

Synonyms:142924-31-0;Ethyl 4,6-O-[(R)-phenylmethylene]-1-thio-alpha-D-mannopyranoside;Ethyl 4,6-O-benzylidene-D-thiomannopyranoside;DTXSID701187070;(2R,4aR,6R,7S,8R,8aS)-6-ethylsulfanyl-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

Chemical Property of Ethyl 4,6-O-benzylidene-D-thiomannopyranoside

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 312.10314491
• Heavy Atom Count: 21
• Complexity: 336

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCSC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)O)O
• Isomeric SMILES: CCS[C@@H]1[C@H]([C@H]([C@H]2[C@H](O1)CO[C@H](O2)C3=CC=CC=C3)O)O

Technology Process of Ethyl 4,6-O-benzylidene-D-thiomannopyranoside

There total 14 articles about Ethyl 4,6-O-benzylidene-D-thiomannopyranoside 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: 95.0%

benzaldehyde dimethyl acetal (1125-88-8) + ethyl 1-thio-β-D-glucopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) → ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8)

Guidance literature:

With hydrogen cation; In N,N-dimethyl-formamide;

Reference yield: 86.0%

benzaldehyde dimethyl acetal (1125-88-8) + ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5) → ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8)

Guidance literature:

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside; With methanol; sodium methylate; at 20 ℃; for 18h;

benzaldehyde dimethyl acetal; With camphor-10-sulfonic acid; In acetonitrile; at 20 ℃;

DOI:10.1039/d0ob00137f

Reference yield: 78.0%

(2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate (149563-08-6) → ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside (20701-61-5,56119-28-9,131564-36-8,142924-31-0,151123-92-1,141899-53-8)

Guidance literature:

With triethylamine; In methanol; water; at 150 ℃; for 0.25h; microwave irradiation;

DOI:10.1081/CAR-100105712

upstream raw materials:

benzaldehyde dimethyl acetal

ethyl 1-thio-β-D-glucopyranoside

(2R,4aR,6S,7R,8S,8aR)-6-(ethylthio)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl dibenzoate

benzaldehyde

Downstream raw materials:

ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

ethyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside