(2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate

Base Information

• Chemical Name: (2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate
• CAS No.: 817197-67-4
• Molecular Formula: C₁₈H₂₂O₇S
• Molecular Weight: 382.434

Synonyms:(2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate

Chemical Property of (2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate

Chemical Property:

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Technology Process of (2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate

There total 2 articles about (2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate 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: 97.0%

para-thiocresol (106-45-6) + 1,2,3,5-tetraacetylribose (13035-61-5) → (2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate (817197-67-4)

Guidance literature:

With indium(III) bromide; In dichloromethane; at 20 ℃; for 2h; stereoselective reaction;

DOI:10.1055/s-0036-1588507

Reference yield:

para-thiocresol (106-45-6) + 1,2,3,5-tetraacetylribose (13035-61-5) → (2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate (817197-67-4) + p-tolyl 2,3,5-tri-O-acetyl-1-thio-α-D-ribofuranoside

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 0 ℃; optical yield given as %de;

DOI:10.1021/jo801408x

Reference yield: 83.0%

(2R,5S)-2-(acetoxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate (817197-67-4) → (2R,5S)-2-(hydroxymethyl)-5-(p-tolylthio)tetrahydrofuran-3,4-diyl diacetate

Guidance literature:

With [^tBu₂Sn(OH)Cl]₂; In tetrahydrofuran; methanol; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.mex.2019.09.031

upstream raw materials:

para-thiocresol

1,2,3,5-tetraacetylribose

Downstream raw materials:

p-tolyl 1-thio-β-D-ribofuranoside

(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl diacetate

N⁴-benzoyl-1-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-cytosine

Tri-O-acetyluridine

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