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

Base Information

• Chemical Name: (2S,3R,4S,5S,6S)-2-(4-formylphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 148579-56-0
• Molecular Formula: C₂₀H₂₂O₁₁
• Molecular Weight: 438.388
• Mol file: 148579-56-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2S,3R,4S,5S,6S)-2-(4-formylphenoxy)-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: 97.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → (2S,3R,4S,5S,6S)-2-(4-formylphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-56-0)

Guidance literature:

With silver(l) oxide; In acetonitrile; at 20 ℃; for 20h; Darkness; Inert atmosphere;

Reference yield: 69.0%

2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester (6919-98-8) + 4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → (2S,3R,4S,5S,6S)-2-(4-formylphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-56-0)

Guidance literature:

With silver(l) oxide; In acetonitrile; at 20 ℃; for 3h; Molecular sieve; Inert atmosphere;

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-(4-formylphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (148579-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: TiBr₄ / CH₂Cl₂ / 24 h / 20 °C

2: Ag₂O / acetonitrile / 2 h / 20 °C

With titanium(IV) bromide; silver(l) oxide; In dichloromethane; acetonitrile; 1: Bromination / 2: Addition;

DOI:10.1021/jm990124q

upstream raw materials:

4-hydroxy-benzaldehyde

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

2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester

methyl D-glucopyranuronate

Downstream raw materials:

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

methyl 1-(4-hydroxymethylphenyl)-β-D-glucopyranuronate

methyl N-[9-(β-D-glucuronyl)benzyloxycarbonyl]aminocamptothecin

(2S,3R,4S,5S,6S)-2-(4-((4-(difluoromethyl)phenylcarbamoyloxy)methyl)phenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate