(2R,3S)-5α-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate

Base Information

• Chemical Name: (2R,3S)-5α-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate
• CAS No.: 316354-49-1
• Molecular Formula: C₂₁H₂₁N₃O₅
• Molecular Weight: 395.415

Synonyms:(2R,3S)-5α-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate

Chemical Property of (2R,3S)-5α-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3S)-5α-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate

There total 5 articles about (2R,3S)-5α-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate 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:

2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (52162-55-7,69256-45-7,61826-14-0) → (2R,3S)-5β-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate (234106-08-2) + (2R,3S)-5α-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate (316354-49-1)

Guidance literature:

With cesium azide; In dimethyl sulfoxide; at 20 ℃; Overall yield = 90 %; Overall yield = 1.37 g; Optical yield = 81.818 %de;

DOI:10.1039/c6ob00500d

Reference yield:

Hoffer's chlorosugar (3601-89-6,4330-21-6,52304-86-6,3056-12-0,141846-57-3) → (2R,3S)-5β-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate (234106-08-2) + (2R,3S)-5α-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate (316354-49-1)

Guidance literature:

With lithium azide; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 2h;

DOI:10.1002/cbdv.201000047

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → (2R,3S)-5α-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate (316354-49-1)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride / water / 20 °C

2: dmap; pyridine / 12 h / 0 °C

3: hydrogenchloride / diethyl ether / 0 °C

4: boron trifluoride diethyl etherate; trimethylsilylazide / dichloromethane / 0 °C

With pyridine; hydrogenchloride; dmap; trimethylsilylazide; boron trifluoride diethyl etherate; In diethyl ether; dichloromethane; water;

DOI:10.1021/jo302033f

upstream raw materials:

Hoffer's chlorosugar

D-2-deoxyribose

1-O-methyl-2-deoxy-D-ribofuranoside

methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose

Downstream raw materials:

1-[O³,O⁵-bis-(4-methyl-benzoyl)-β-D-erythro-2-deoxy-pentofuranosyl]-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

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