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

Base Information

• Chemical Name: (2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 148579-83-3
• Molecular Formula: C₂₀H₂₁NO₁₃
• Molecular Weight: 483.386
• Mol file: 148579-83-3.mol

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

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

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 70.0%

5-Nitrosalicylaldehyde (97-51-8) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → (2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-83-3)

Guidance literature:

With silver(l) oxide; In acetonitrile; for 4h; Ambient temperature;

DOI:10.1021/jm970589l

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester (7355-18-2) → (2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: titanium(IV) bromide / dichloromethane / 8 h / 20 °C / Cooling with ice

2: silver(l) oxide / acetonitrile / 16 h / 0 - 20 °C / Cooling with ice

With titanium(IV) bromide; silver(l) oxide; In dichloromethane; acetonitrile;

Reference yield:

D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) → (2S,3R,4S,5S,6S)-2-(2-formyl-4-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 20 °C

1.2: Cooling with ice

2.1: titanium(IV) bromide / dichloromethane / 24 h / 20 °C

3.1: silver(l) oxide / acetonitrile / 20 °C

With titanium(IV) bromide; silver(l) oxide; In dichloromethane; acetonitrile;

DOI:10.1021/ja209335z

upstream raw materials:

5-Nitrosalicylaldehyde

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

D-glucurono-6,3-lactone

(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Downstream raw materials:

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

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

methyl 1-O-(2-difluoromethyl-4-nitrophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

methyl 1-O-(2-difluoromethyl-4-aminophenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate