alpha-L-arabino-Hexopyranoside, phenyl 2,6-dideoxy-1-thio-, 3,4-diacetate

Base Information

• Chemical Name: alpha-L-arabino-Hexopyranoside, phenyl 2,6-dideoxy-1-thio-, 3,4-diacetate
• CAS No.: 135197-78-3
• Molecular Formula: C₁₆H₂₀O₅S
• Molecular Weight: 324.398
• DSSTox Substance ID: DTXSID701156198

Synonyms:DTXSID701156198;alpha-L-arabino-Hexopyranoside, phenyl 2,6-dideoxy-1-thio-, 3,4-diacetate;135197-78-3

Chemical Property of alpha-L-arabino-Hexopyranoside, phenyl 2,6-dideoxy-1-thio-, 3,4-diacetate

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 324.10314491
• Heavy Atom Count: 22
• Complexity: 394

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(CC(O1)SC2=CC=CC=C2)OC(=O)C)OC(=O)C
• Isomeric SMILES: C[C@H]1[C@@H]([C@H](C[C@@H](O1)SC2=CC=CC=C2)OC(=O)C)OC(=O)C

Technology Process of alpha-L-arabino-Hexopyranoside, phenyl 2,6-dideoxy-1-thio-, 3,4-diacetate

There total 9 articles about alpha-L-arabino-Hexopyranoside, phenyl 2,6-dideoxy-1-thio-, 3,4-diacetate 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: 99.0%

acetic anhydride (108-24-7) + (2R,3R,4R)-2-Methyl-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol (141805-54-1) → Acetic acid (2R,3S,4R)-3-acetoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester (135197-78-3,135197-79-4,135197-83-0,135197-84-1,139190-73-1,139190-76-4,139241-86-4)

Guidance literature:

With pyridine; dmap; at 25 ℃; for 0.5h;

DOI:10.1016/0040-4039(91)80435-9

Reference yield: 86.0%

phenylthiotrimethylsilane (4551-15-9) + methyl 3,4-di-O-acetyl-2,6-dideoxy-α-D-ribo-hexopyranoside (33650-60-1) → Acetic acid (2R,3R,4S)-3-acetoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester (135197-78-3,135197-79-4,135197-83-0,135197-84-1,139190-73-1,139190-76-4,139241-86-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 25 ℃; for 1h;

DOI:10.1016/0040-4039(91)80435-9

Reference yield: 82.0%

3,4-di-O-acetyl-1-O-tert-butyldimethylsilyl-2,6-dideoxy-β-L-lyxo-hexopyranose (128135-55-7) + thiophenol (108-98-5) → Acetic acid (2S,3R,4S)-3-acetoxy-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester (135197-78-3,135197-79-4,135197-83-0,135197-84-1,139190-73-1,139190-76-4,139241-86-4)

Guidance literature:

With zirconium(IV) chloride;

DOI:10.1016/S0040-4039(00)71241-X

upstream raw materials:

3,4-di-O-acetyl-1-O-tert-butyldimethylsilyl-2,6-dideoxy-β-L-lyxo-hexopyranose

thiophenol

3,4-Di-O-acetyl-2,6-dideoxy-L-lyxo-hexopyranose

phenylthiotrimethylsilane

Downstream raw materials:

Acetic acid (2R,3R,4S,6R)-3-acetoxy-6-cyclohexylmethoxy-2-methyl-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3R,4S,6S)-3-acetoxy-6-cyclohexylmethoxy-2-methyl-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R,6R)-3-acetoxy-6-cyclohexylmethoxy-2-methyl-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R,6S)-3-acetoxy-6-cyclohexylmethoxy-2-methyl-tetrahydro-pyran-4-yl ester

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