Methyl-2-deoxy-alpha-L-erythro-pentofuranose

Base Information

• Chemical Name: Methyl-2-deoxy-alpha-L-erythro-pentofuranose
• CAS No.: 144301-84-8
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.159
• Mol file: 144301-84-8.mol

Synonyms:Methyl-2-deoxy-alpha-L-erythro-pentofuranose;

Chemical Property of Methyl-2-deoxy-alpha-L-erythro-pentofuranose

Chemical Property:

• Refractive Index: 1.487
• Boiling Point: 294.492 °C at 760 mmHg
• PKA: 13.81±0.60(Predicted)
• Flash Point: 131.904 °C
• PSA: 58.92000
• Density: 1.245 g/cm³
• LogP: -0.89900

Purity/Quality:

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

METHYL-2-DEOXY-ALPHA-L-ERYTHRO-PENTOFURANOSE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl-2-deoxy-alpha-L-erythro-pentofuranose

There total 20 articles about Methyl-2-deoxy-alpha-L-erythro-pentofuranose 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、 Jandu,Selwood. "4'-Thionucleosides via in situ pyranose-furanose rearrangements: A short synthesis of the antiherpes agent 2'-deoxy-5-ethyl-4'-thiouridine via direct coupling of a silylated pyrimidine base with a 4-thiopyranose sugar". . p. 5170 - 5173. Retrieved 1995.
• 2、 Minuth, Marco,Richert, Clemens. "A nucleobase analogue that pairs strongly with adenine". . p. 10874 - 10877. Retrieved 2013.
• 3、 -. "2-deoxy-D-ribose derivative". Paragraph 0048-0050; 0055-0057. . Retrieved 2020/08/09.
• 4、 Shiozaki, Yoko,Sakurai, Shunya,Sakamoto, Ryu,Matsumoto, Akira,Maruoka, Keiji. "Iron-Catalyzed Radical Cleavage/C?C Bond Formation of Acetal-Derived Alkylsilyl Peroxides". supporting information. p. 573 - 576. Retrieved 2020/02/20.