(2S,3R,4R,5R)-5-Methyltetrahydrofuran-2,3,4-triyl triacetate

Base Information

• Chemical Name: (2S,3R,4R,5R)-5-Methyltetrahydrofuran-2,3,4-triyl triacetate
• CAS No.: 27821-07-4
• Molecular Formula: C₁₁H₁₆O₇
• Molecular Weight: 260.244
• Mol file: 27821-07-4.mol

Synonyms:beta-D-5-Deoxyxylofuranose triacetate

Chemical Property of (2S,3R,4R,5R)-5-Methyltetrahydrofuran-2,3,4-triyl triacetate

Chemical Property:

• Boiling Point: 315℃
• Flash Point: 136℃
• PSA: 88.13000
• Density: 1.23
• LogP: 0.15770

Purity/Quality:

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

(2S,3R,4S,5R)-5-Methyltetrahydrofuran-2,3,4-triyl triacetate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: β-D-5-Deoxy-xylofuranose Triacetate is used in the synthesis of nucleotide derivatives. Primarily studied in the understanding of long range σ-coupling properties.

Technology Process of (2S,3R,4R,5R)-5-Methyltetrahydrofuran-2,3,4-triyl triacetate

There total 36 articles about (2S,3R,4R,5R)-5-Methyltetrahydrofuran-2,3,4-triyl triacetate 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: 86.68%

5'-deoxyinosine + acetic anhydride (108-24-7) → 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose (27821-07-4,27930-18-3,37076-71-4,62211-93-2,63903-44-6,76497-54-6)

Guidance literature:

for 9h; Reflux;

Reference yield: 86.4%

(2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol (279673-09-5,947605-23-4) + acetic anhydride (108-24-7) → 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose (27821-07-4,27930-18-3,37076-71-4,62211-93-2,63903-44-6,76497-54-6)

Guidance literature:

With dmap; triethylamine; at -5 - 5 ℃; for 4h;

Reference yield: 76.5%

5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose (37076-71-4) → 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose (27821-07-4,27930-18-3,37076-71-4,62211-93-2,63903-44-6,76497-54-6)

Guidance literature:

In hexane; isopropyl alcohol; at -10 - 5 ℃; for 3h; Purification / work up;

upstream raw materials:

5-O-deoxy-D-ribofuranose

acetic anhydride

5′-deoxyribose

methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside

Downstream raw materials:

(2R,3R,4R,5R)-2-(4-amino-5-fluoro-2-oxopyrimidin-1(2H)-yl)-5-methyl-tetrahydrofuran-3,4-diyl diacetate

Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[5-fluoro-2-oxo-4-(3,4,5-trimethoxy-benzoylamino)-2H-pyrimidin-1-yl]-5-methyl-tetrahydro-furan-3-yl ester

N¹-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-5-fluoro-N⁴-(pentyloxycarbonyl)cytosine

capecitabine

Refernces

• 1、 -. "AMPHIPHILE PRODRUGS". . . Retrieved 2019/06/12.
• 2、 -. "A three-acetyl deoxyribose α isomer preparation method". Paragraph 0015; 0016. . Retrieved 2019/07/04.