2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribonic acid-1,4-lactone

Base Information

• Chemical Name: 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribonic acid-1,4-lactone
• CAS No.: 7392-74-7
• Molecular Formula: C27H22 O8
• Molecular Weight: 474.467
• Hs Code.: 2932209090
• Mol file: 7392-74-7.mol

Synonyms:D-ribo-Pentonicacid, 2-C-methyl-, g-lactone, tribenzoate (7CI); Ribonic acid, 2-C-methyl-, g-lactone, tribenzoate, D- (8CI)

Chemical Property of 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribonic acid-1,4-lactone

Chemical Property:

• Melting Point: 131-133oC
• Boiling Point: 589.0±39.0 °C(Predicted)
• PSA: 105.20000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 3.61010
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribonic acid-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribonic-1,4-lactone (cas# 7392-74-7) is a compound useful in organic synthesis.

Technology Process of 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribonic acid-1,4-lactone

There total 11 articles about 2,3,5-Tri-O-benzoyl-2-C-methyl-D-ribonic acid-1,4-lactone 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: 95.0%

2-C-methyl-D-ribono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7) + benzoyl chloride (98-88-4) → (3R,4R,5R)-5-((benzoyloxy)methyl)-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate (7392-74-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/acsmedchemlett.5b00402

Reference yield: 86.0%

benzoyl chloride (98-88-4) + 2-C-methyl-DL-lyxono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7) → C27H22O8 (7392-74-7,36792-00-4,36792-01-5,93635-77-9,93636-13-6,93636-17-0,94008-76-1)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1016/0008-6215(84)85302-1

Reference yield: 84.0%

benzoyl chloride (98-88-4) + 2-C-methyl-DL-arabinono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7) → C27H22O8 (7392-74-7,36792-00-4,36792-01-5,93635-77-9,93636-13-6,93636-17-0,94008-76-1)

Guidance literature:

With pyridine;

DOI:10.1016/0008-6215(84)85302-1

upstream raw materials:

2-C-methyl-D-ribono-1,4-lactone

benzoyl chloride

2-C-methyl-DL-arabinono-1,4-lactone

ethyl trans-2,3-dideoxy-4,5-O-isopropylidene-2-C-methyl-DL-glycero-pent-2-enonate

Downstream raw materials:

(2R,3R,4R,5R)-2-(2-amino-6-chloro-9H-purin-9-yl)-5-(benzoyloxymethyl)-3-methyltetrahydrofuran-3,4-diyl dibenzoate

C₃₆H₃₆N₅O₁₀P

2,6-dichloro-9-(2-C-methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine

2-methyl-2,3,5-tribenzoyl-ribonolactol

Refernces

• 1、 -. "A (2 'R) -2' - deoxy -2 '- fluoro -2' - methyl urea glucoside preparation method (by machine translation)". Paragraph 0029. . Retrieved 2017/02/28.
• 2、 Aparicio, Fidel J. Lopez,Cubero, Isidoro Izquierdo,Olea, Maria D. Portal. "SYNTHESIS OF SACCHARINIC ACID DERIVATIVES". . p. 99 - 110. Retrieved 2007/10/02.