((2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl)methyl benzoate

Base Information

• Chemical Name: ((2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl)methyl benzoate
• CAS No.: 122111-01-7
• Molecular Formula: C19H14F2O6
• Molecular Weight: 376.313
• Hs Code.: 29322090
• DSSTox Substance ID: DTXSID50431340
• Nikkaji Number: J465.929E
• Wikidata: Q72462085
• Mol file: 122111-01-7.mol

Synonyms:122111-01-7;((2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl)methyl benzoate;2-Deoxy-2,2-difluoro-D-erythro-pentafuranous-1-ulose-3,5-dibenzoate;2-Deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate;2-Deoxyl-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate;2-Deoxy-2,2-difluoro-D-erythro-pentonic acid gamma lactone 3,5-dibenzoate;(2R,3R)-2-[(benzoyloxy)methyl]-4,4-difluoro-5-oxooxolan-3-yl benzoate;MFCD08458308;C19H14F2O6;SCHEMBL881734;3,5-Bis(benzoyl)-2-deoxy-2,2-difluoro-1-oxoribose;DTXSID50431340;D-erythro-Pentonicacid, 2-deoxy-2,2-difluoro--lactone,3,5-dibenzoate;AKOS015965558;D-erythro-Pentonic acid, 2-deoxy-2,2-difluoro-, g-lactone,3,5-dibenzoate;AC-4262;AS-11434;CS-0031397;EN300-7391686;A804844;3-O,5-O-Dibenzoyl-2-deoxy-2,2-difluoro-D-ribonic acid lactone;[(2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxooxolan-2-yl]methyl benzoate (non-preferred name)

Chemical Property of ((2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl)methyl benzoate

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 7.61E-08mmHg at 25°C
• Melting Point: 117-119 °C(lit.)
• Refractive Index: 1.57
• Boiling Point: 437.216 °C at 760 mmHg
• Flash Point: 210.499 °C
• PSA: 78.90000
• Density: 1.41 g/cm³
• LogP: 2.62970
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 376.07584449
• Heavy Atom Count: 27
• Complexity: 567

Purity/Quality:

99% ^*data from raw suppliers

3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-D-ribonic acid-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC2C(C(C(=O)O2)(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(=O)O2)(F)F)OC(=O)C3=CC=CC=C3
• Uses: 2-Deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate (CAS: 122111-01-7) is a compound useful in organic synthesis and it is the key intermediate of gemcitabine. 2-Deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate (cas# 122111-01-7) is a compound useful in organic synthesis.

Technology Process of ((2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl)methyl benzoate

There total 10 articles about ((2R,3R)-3-(Benzoyloxy)-4,4-difluoro-5-oxotetrahydrofuran-2-yl)methyl benzoate 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: 67.0%

benzoyl chloride (98-88-4) + 2-deoxy-2,2-difluoro-1-carbonylribose (95058-77-8) → 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 1.5h; Reflux;

Reference yield: 34.0%

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate (122111-02-8) + C19H16F2O7 (866473-33-8) → 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8)

Guidance literature:

toluene-4-sulfonic acid; In toluene; Product distribution / selectivity; Heating / reflux; Dean and Stark apparatus;

Reference yield:

2-deoxy-2,2-difluoropentofuranos-1-ulose + benzoyl chloride (98-88-4) → 2-deoxy-2,2-difluoro-D-erythro-pentonic acid γ-lactone 3,5-dibenzoate (122111-01-7,122111-02-8)

Guidance literature:

With pyridine; In ethyl acetate; at 25 - 60 ℃; Inert atmosphere;

upstream raw materials:

benzoyl chloride

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

2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-dibenzoate

C₁₉H₁₆F₂O₇

Downstream raw materials:

C₁₉H₁₆F₂O₆

(2R,3R)-2-((benzoyloxy)methyl)-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate

Refernces

• 1、 -. "Method for synthesizing 2- deoxy -2,2- difluoropentanoic acid -1- ketone -3,5- dibenzoin (by machine translation)". Paragraph 0058-0061. . Retrieved 2020/03/09.
• 2、 Chen, Zhe,Ku, Therese C.,Seley-Radtke, Katherine L.. "Thiophene-expanded guanosine analogues of Gemcitabine". . p. 4274 - 4276. Retrieved 2020/12/14.