a-D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate

Base Information

• Chemical Name: a-D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate
• CAS No.: 143157-22-6
• Molecular Formula: C₁₉H₁₆F₂O₆
• Molecular Weight: 378.329
• DSSTox Substance ID: DTXSID201172131
• Mol file: 143157-22-6.mol

Synonyms:a-D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate;3,5-dibenzoate;SCHEMBL2692294;DTXSID201172131;a-D-erythro-Pentofuranose,2-deoxy-2,2-difluoro-,;alpha-D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate;[(2R,3R,5S)-3-(benzoyloxy)-4,4-difluoro-5-hydroxyoxolan-2-yl]methyl benzoate

Chemical Property of a-D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.579
• Boiling Point: 495.925 °C at 760 mmHg
• PKA: 9.95±0.70(Predicted)
• Flash Point: 253.726 °C
• PSA: 82.06000
• Density: 1.41 g/cm³
• LogP: 2.42150
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 378.09149455
• Heavy Atom Count: 27
• Complexity: 528

Purity/Quality:

99% ^*data from raw suppliers

3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(O2)O)(F)F)OC(=O)C3=CC=CC=C3
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H](C([C@H](O2)O)(F)F)OC(=O)C3=CC=CC=C3

Technology Process of a-D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate

There total 17 articles about a-D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 3,5-dibenzoate 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%

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8) → (2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate (1173824-58-2,143157-25-9,143157-22-6)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; diethyl ether; at 10 - 30 ℃; for 1h;

DOI:10.1055/s-1992-26167

Reference yield: 33.0%

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentono-γ-lactone (197452-15-6,122111-02-8) → 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-L-erythro-pentofuranose (143157-25-9,143157-22-6)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at -50 ℃; for 0.666667h;

DOI:10.1021/jm970275y

Reference yield:

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8) → 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-D-β-ribofuranose (143157-25-9,143157-22-6) + 3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-D-α-ribofuranose (143157-25-9,143157-22-6)

Guidance literature:

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate; With sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; toluene; at -70 - -50 ℃; for 1h;

With hydrogenchloride; methanol; water; In tetrahydrofuran; toluene; for 0.5h;

upstream raw materials:

2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate

benzoyl chloride

2-deoxy-2,2-difluoro-1-carbonylribose

ethyl (3R,S)-2,2-difluoro-3-hydroxy-(2,2-dimethyldioxolpent-4-yl)propionate

Downstream raw materials:

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)thymine

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-chlorouracil

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-bromouracil

1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-D-erythro-pentofuranos-1-yl)-5-iodouracil

Refernces

• 1、 -. "Method for recovering mother liquor of gemcitabine intermediate". Paragraph 0059-0060; 0068. . Retrieved 2021/06/22.
• 2、 Liu, Tongchao,Tang, Jiadeng,Liang, Jianpeng,Chen, Yabin,Wang, Xiaowen,Shen, Jingkang,Zhao, Dongmei,Xiong, Bing,Cen, Jun-Da,Chen, Yue-Lei. "Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine". . p. 1203 - 1213. Retrieved 2019/01/29.