Benzoic acid (2R,3S,4R,6R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R,6R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 325475-00-1
• Molecular Formula: C₁₅H₁₇N₃O₅
• Molecular Weight: 319.317
• Mol file: 325475-00-1.mol

Synonyms:Benzoic acid (2R,3S,4R,6R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2R,3S,4R,6R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R,6R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester

There total 4 articles about Benzoic acid (2R,3S,4R,6R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester 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: 91.0%

acetyl 4-O-benzoyl-3-O-methanesulfonyl-2,6-dideoxy-α-D-ribo-hexopyranosside (325474-97-3) → Benzoic acid (2R,3S,4R,6R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester (325475-00-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 75 ℃; for 34h;

DOI:10.1016/S0040-4020(00)00868-1

Reference yield:

Benzoic acid (2S,3R,4S,6S)-2-bromomethyl-4-methanesulfonyloxy-6-methoxy-tetrahydro-pyran-3-yl ester (72062-67-0) → Benzoic acid (2R,3S,4R,6R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester (325475-00-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / H₂; Et₃N / Raney nickel / methanol; H₂O / 12 h / 20 °C

2: 84 percent / aq. HOAc; aq. HCl / 1.5 h / Heating

3: 87 percent / pyridine / 14 h / 0 °C

4: 91 percent / NaN₃ / dimethylformamide / 34 h / 75 °C

With pyridine; hydrogenchloride; sodium azide; hydrogen; acetic acid; triethylamine; nickel; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(00)00868-1

Reference yield:

4-O-benzoyl-3-O-methanesulfonyl-2,6-dideoxy-α-D-ribo-hexopyranose (325474-95-1) → Benzoic acid (2R,3S,4R,6R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester (325475-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / pyridine / 14 h / 0 °C

2: 91 percent / NaN₃ / dimethylformamide / 34 h / 75 °C

With pyridine; sodium azide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(00)00868-1

upstream raw materials:

acetyl 4-O-benzoyl-3-O-methanesulfonyl-2,6-dideoxy-α-D-ribo-hexopyranosside

Benzoic acid (2S,3R,4S,6S)-2-bromomethyl-4-methanesulfonyloxy-6-methoxy-tetrahydro-pyran-3-yl ester

4-O-benzoyl-3-O-methanesulfonyl-2,6-dideoxy-α-D-ribo-hexopyranose

methyl 4-O-benzoyl-3-O-methanesulfonyl-2,6-dideoxy-α-D-ribo-hexopyranoside

Downstream raw materials:

Benzoic acid (2R,3S,4R,6R)-4-azido-6-(1-hydroxy-6,8-dimethoxy-3-methyl-7,12-dioxo-7,12-dihydro-benzo[a]anthracen-2-yl)-2-methyl-tetrahydro-pyran-3-yl ester