Phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside

Base Information

• Chemical Name: Phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside
• CAS No.: 183075-04-9
• Molecular Formula: C₁₁H₁₄O₃S
• Molecular Weight: 226.296
• DSSTox Substance ID: DTXSID001240704
• Nikkaji Number: J774.701B
• Mol file: 183075-04-9.mol

Synonyms:DTXSID001240704;Phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside;1-(Phenylthio)-1,2-dideoxy-D-erythro-pentofuranose;183075-04-9

Chemical Property of Phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 226.06636548
• Heavy Atom Count: 15
• Complexity: 194

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(C(OC1SC2=CC=CC=C2)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](OC1SC2=CC=CC=C2)CO)O

Technology Process of Phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside

There total 3 articles about Phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside 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: 97.0%

2-Deoxy-D-ribose (533-67-5) + thiophenol (108-98-5) → phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside (183075-04-9)

Guidance literature:

With sulfuric acid; In N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2010.04.043

Reference yield: 16.0%

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) + thiophenol (108-98-5) → phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside (183075-04-9) + (3R,4S)-6-Phenylsulfanyl-tetrahydro-pyran-3,4-diol + (2R,3S)-5,5-Bis-phenylsulfanyl-pentane-1,2,3-triol

Guidance literature:

With hydrogenchloride; Yields of byproduct given; Ambient temperature;

DOI:10.1016/0040-4039(96)01293-2

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) + thiophenol (108-98-5) → phenyl 2-deoxy-1-thio-D-erythro-pentofuranoside (183075-04-9) + (3R,4S)-6-Phenylsulfanyl-tetrahydro-pyran-3,4-diol

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1016/0040-4039(96)01293-2

upstream raw materials:

D-2-deoxyribose

thiophenol

2-Deoxy-D-ribose

Downstream raw materials:

(2R,3S)-5-Phenylsulfanyl-2-trityloxymethyl-tetrahydro-furan-3-ol

phenyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-deoxy-1-thio-D-erythro-pentofuranoside

phenyl 3,5-O-(di-tert-butylsilylene)-1-thio-D-erythro-furanoside

(S)-2-Phenylsulfanyl-5-trityloxymethyl-2,5-dihydro-furan