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

Base Information

• Chemical Name: (2R,3S)-5β-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate
• CAS No.: 234106-08-2
• Molecular Formula: C₂₁H₂₁N₃O₅
• Molecular Weight: 395.415

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

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

Chemical Property:

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

There total 9 articles about (2R,3S)-5β-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: 90.0%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → (2R,3S)-5β-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate (234106-08-2)

Guidance literature:

With cesium azide; In dimethyl sulfoxide;

DOI:10.1039/c3ra44120b

Reference yield:

C23H24O7 (57236-72-3) → (2R,3S)-5β-azido-2-{[(4-methylbenzoyl)oxy]methyl}tetrahydrofuran-3-yl 4-methylbenzoate (234106-08-2)

Guidance literature:

With trimethylsilylazide; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 3h;

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

upstream raw materials:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

Hoffer's chlorosugar

D-2-deoxyribose

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

Downstream raw materials:

1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(phenanthren-9-yl)-1H-1,2,3-triazole

1-(2′-deoxy-β-D-ribofuranosyl)-4-(3,5-dimethoxyphenyl)-1H-1,2,3-triazole

1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(3,5-dimethoxyphenyl)-1H-1,2,3-triazole

1-[2′-deoxy-3′,5′-bis{O-(p-toluoyl)}-β-D-ribofuranosyl]-4-(4-nitrophenyl)-1H-1,2,3-triazole

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