(2R,3S,5S)-2-(hydroxymethyl)-5-methoxyoxolan-3-ol

Base Information

• Chemical Name: (2R,3S,5S)-2-(hydroxymethyl)-5-methoxyoxolan-3-ol
• CAS No.: 51255-17-5
• Molecular Formula: C6H12 O4
• Molecular Weight: 148.16
• Hs Code.: 2932190090
• DSSTox Substance ID: DTXSID801267437
• Nikkaji Number: J344.429E
• Mol file: 51255-17-5.mol

Synonyms:51255-17-5;Methyl-2-deoxy-alpha-D-ribofuranoside;(2R,3S,5S)-2-(hydroxymethyl)-5-methoxyoxolan-3-ol;Methyl 2-deoxy-a-D-ribofuranoside;Methyl-2-deoxy-|A-D-ribofuranoside;methyl 2-deoxy-alpha-D-erythro-pentofuranoside;51255-18-6;SCHEMBL2817760;DTXSID801267437;Methyl 2-deoxy-|A-D-ribofuranoside;AKOS006288995;Methyl 2-deoxy-alpha-D-ribofuranoside;W-202930;(2R,3S,5S)-2-(Hydroxymethyl)-5-methoxytetrahydrofuran-3-ol

Chemical Property of (2R,3S,5S)-2-(hydroxymethyl)-5-methoxyoxolan-3-ol

Chemical Property:

• Refractive Index: 1.487
• Boiling Point: 294.5±40.0 °C(Predicted)
• PKA: 13.81±0.60(Predicted)
• PSA: 58.92000
• Density: 1.24 g/cm³
• LogP: -0.89900
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 148.07355886
• Heavy Atom Count: 10
• Complexity: 106

Purity/Quality:

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

Methyl 2-deoxy-a-D-ribofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1CC(C(O1)CO)O
• Isomeric SMILES: CO[C@@H]1C[C@@H]([C@H](O1)CO)O

Technology Process of (2R,3S,5S)-2-(hydroxymethyl)-5-methoxyoxolan-3-ol

There total 32 articles about (2R,3S,5S)-2-(hydroxymethyl)-5-methoxyoxolan-3-ol 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: 100.0%

methanol (67-56-1) + D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9)

Guidance literature:

sulfuric acid; Ambient temperature;

DOI:10.1016/S0040-4039(00)96753-4

Reference yield: 100.0%

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) + acetyl chloride (75-36-5) → 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9)

Guidance literature:

In methanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2013.08.038

Reference yield: 100.0%

methanol (67-56-1) + 2-Deoxy-D-ribose (533-67-5) → 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja8043695

upstream raw materials:

2-Deoxy-D-ribose

methanol

2-deoxy-D-ribose

(2R,3S)-2-(hydroxymethyl)tetrahydrofuran-3-ol

Downstream raw materials:

methyl 2-deoxy-3,5-di-O-p-toluenesulfonyl-D-erythro-pentofuranoside

methyl 2-deoxy-β-D-erythro-pentopyranoside

methyl 3,5-dibenzoyloxy-2-deoxy-β-D-erythropentofuranoside

methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside

Refernces

• 1、 -. "Purification method of decitabine intermediate". Paragraph 0038; 0039. . Retrieved 2020/07/24.
• 2、 Wishka, Donn G.,Lopez, Omar D.,Rudchenko, Vladimir F.,Huang, Guangfei,Bahde, Robert,Kumar, Vineet,Denysenko, Sergiy M.,Zhang, Lianhao,Zhang, Mianji,Teicher, Beverly A.,Morris, Joel. "The development of β-selective glycosylation reactions with benzyl substituted 2-deoxy-1,4-dithio-D-erythro-pentofuranosides: enabling practical multi-gram syntheses of 4'-Thio-2'-deoxycytidine (T-dCyd) and 5-aza-4’-thio-2’-deoxycytidine (aza-T-dCyd) to s". . p. 68 - 95. Retrieved 2020/10/21.