(2R,3R,4R,5R)-2-[(4-chlorobenzoyloxy)methyl]-4-fluoro-5-hydroxy-4-methyloxolan-3-yl 4-chlorobenzoate

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-[(4-chlorobenzoyloxy)methyl]-4-fluoro-5-hydroxy-4-methyloxolan-3-yl 4-chlorobenzoate
• CAS No.: 1294481-80-3
• Molecular Formula: C₂₀H₁₇Cl₂FO₆
• Molecular Weight: 443.256
• Mol file: 1294481-80-3.mol

Synonyms:1294481-80-3;(2R,3R,4R,5R)-2-[(4-chlorobenzoyloxy)methyl]-4-fluoro-5-hydroxy-4-methyloxolan-3-yl 4-chlorobenzoate;beta-D-erythro-Pentofuranose, 2-deoxy-2-fluoro-2-methyl-, 3,5-bis(4-chlorobenzoate), (2R)-;SCHEMBL2481853;VMHGRJLDOZXGNA-XNFNUYLZSA-N;CS-0185099;P12937;((2R,3R,4R,5R)-3-(4-chlorobenzoyloxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl 4-chlorobenzoate;(2R,3R,4R,5R)-2-[(4-chlorobenzoyloxy)methyl]-4-fluoro-5-hydroxy-4-methyloxolan-3-yl4-chlorobenzoate

Chemical Property of (2R,3R,4R,5R)-2-[(4-chlorobenzoyloxy)methyl]-4-fluoro-5-hydroxy-4-methyloxolan-3-yl 4-chlorobenzoate

Chemical Property:

• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 442.0386218
• Heavy Atom Count: 29
• Complexity: 592

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C(C(OC1O)COC(=O)C2=CC=C(C=C2)Cl)OC(=O)C3=CC=C(C=C3)Cl)F
• Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1O)COC(=O)C2=CC=C(C=C2)Cl)OC(=O)C3=CC=C(C=C3)Cl)F

Technology Process of (2R,3R,4R,5R)-2-[(4-chlorobenzoyloxy)methyl]-4-fluoro-5-hydroxy-4-methyloxolan-3-yl 4-chlorobenzoate

There total 3 articles about (2R,3R,4R,5R)-2-[(4-chlorobenzoyloxy)methyl]-4-fluoro-5-hydroxy-4-methyloxolan-3-yl 4-chlorobenzoate 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: 61.0%

((2R,3R,4R) 3-(4-chlorobenzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl-4-chlorobenzoate (1294481-79-0) → ((2R,3R,4R,5R)-3-((4-chlorobenzoyl)oxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl 4-chlorobenzoate (1294481-80-3)

Guidance literature:

((2R,3R,4R) 3-(4-chlorobenzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl-4-chlorobenzoate; With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at -30 - -10 ℃; for 2.25h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water; ethyl acetate; optical yield given as %de;

DOI:10.1021/jo200060f

Reference yield:

4-chloro-benzoyl chloride (122-01-0) → ((2R,3R,4R,5R)-3-((4-chlorobenzoyl)oxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl 4-chlorobenzoate (1294481-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 20 °C

2: lithium tri(tert-butoxy)aluminum hydride / tetrahydrofuran / 1.33 h / -20 °C

With lithium tri(tert-butoxy)aluminum hydride; triethylamine; In tetrahydrofuran;

Reference yield:

(3R,4R,5R)-3?fluoro?4?hydroxy?5?(hydroxymethyl)?3?methyltetrahydrofuran?2?one (879551-04-9) → ((2R,3R,4R,5R)-3-((4-chlorobenzoyl)oxy)-4-fluoro-5-hydroxy-4-methyltetrahydrofuran-2-yl)methyl 4-chlorobenzoate (1294481-80-3)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 20 °C

2: lithium tri(tert-butoxy)aluminum hydride / tetrahydrofuran / 1.33 h / -20 °C

With lithium tri(tert-butoxy)aluminum hydride; triethylamine; In tetrahydrofuran;

upstream raw materials:

((2R,3R,4R) 3-(4-chlorobenzoyloxy)-4-fluoro-4-methyl-5-oxotetrahydrofuran-2-yl)methyl-4-chlorobenzoate

(3R,4R,5R)-3?fluoro?4?hydroxy?5?(hydroxymethyl)?3?methyltetrahydrofuran?2?one

4-chloro-benzoyl chloride

Downstream raw materials:

(2R,3R,4R,5R)-5-(2-amino-6-ethoxy-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

PSI-938

(2R,3R,4R,5R)-5-bromo-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate

(2R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-2-(((4-chlorobenzoyl)oxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl 4-chlorobenzoate