(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 148579-85-5
• Molecular Formula: C₂₇H₂₆N₂O₁₇
• Molecular Weight: 650.507
• Mol file: 148579-85-5.mol

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 4 articles about (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl 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:

4-Nitrophenyl chloroformate (7693-46-1) + methyl {[2-(hydroxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate (148579-84-4) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester (148579-85-5)

Guidance literature:

With triethylamine; In dichloromethane; acetonitrile; at 0 ℃; for 1.5h;

DOI:10.1021/jm970589l

Reference yield:

5-Nitrosalicylaldehyde (97-51-8) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester (148579-85-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / silver oxide / acetonitrile / 4 h / Ambient temperature

2: 75 percent / NaBH₄, silica gel HL₆₀ / CHCl₃; propan-2-ol / 0.75 h / 0 °C

3: Et₃N / CH₂Cl₂; acetonitrile / 1.5 h / 0 °C

With sodium tetrahydroborate; silica gel; triethylamine; silver(l) oxide; In dichloromethane; chloroform; isopropyl alcohol; acetonitrile;

DOI:10.1021/jm970589l

Reference yield:

(2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-83-3) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-[4-nitro-2-(4-nitro-phenoxycarbonyloxymethyl)-phenoxy]-tetrahydro-pyran-2-carboxylic acid methyl ester (148579-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / NaBH₄, silica gel HL₆₀ / CHCl₃; propan-2-ol / 0.75 h / 0 °C

2: Et₃N / CH₂Cl₂; acetonitrile / 1.5 h / 0 °C

With sodium tetrahydroborate; silica gel; triethylamine; In dichloromethane; chloroform; isopropyl alcohol; acetonitrile;

DOI:10.1021/jm970589l

upstream raw materials:

4-Nitrophenyl chloroformate

methyl {[2-(hydroxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate

5-Nitrosalicylaldehyde

(2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

methyl {[2-(N-benzylcarbamoyloxymethyl)-4-nitrophenyl] 2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate