methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-((4-formylphenylcarbamoyloxy)methyl)phenoxy)-tetrahydro-2H-pyran-2-carboxylate

Base Information

Chemical Name:methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-((4-formylphenylcarbamoyloxy)methyl)phenoxy)-tetrahydro-2H-pyran-2-carboxylate
CAS No.:1349833-42-6
Molecular Formula:C₂₈H₂₉NO₁₃
Molecular Weight:587.537
Hs Code.:

Synonyms:methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-((4-formylphenylcarbamoyloxy)methyl)phenoxy)-tetrahydro-2H-pyran-2-carboxylate

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Chemical Property of methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-((4-formylphenylcarbamoyloxy)methyl)phenoxy)-tetrahydro-2H-pyran-2-carboxylate

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Technology Process of methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-((4-formylphenylcarbamoyloxy)methyl)phenoxy)-tetrahydro-2H-pyran-2-carboxylate

There total 4 articles about methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-((4-formylphenylcarbamoyloxy)methyl)phenoxy)-tetrahydro-2H-pyran-2-carboxylate 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: 82.0%

: 619-66-9
4-Carboxybenzaldehyde

: 148579-57-1
(2S,3R,4S,5S,6S)-2-(4-(hydroxymethyl)phenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 1349833-42-6
methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-((4-formylphenylcarbamoyloxy)methyl)phenoxy)-tetrahydro-2H-pyran-2-carboxylate

Guidance literature:: 4-Carboxybenzaldehyde; With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 25 ℃; Inert atmosphere;

With sodium azide; In acetone; at 0 - 5 ℃; Inert atmosphere;

(2S,3R,4S,5S,6S)-2-(4-(hydroxymethyl)phenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate; Further stages;
DOI:10.1021/jo2018763

Reference yield:

: 123-08-0,65581-83-1
4-hydroxy-benzaldehyde

: 1349833-42-6
methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-((4-formylphenylcarbamoyloxy)methyl)phenoxy)-tetrahydro-2H-pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: silver(l) oxide / acetonitrile / 18 h / 25 °C / Inert atmosphere; Darkness

2.1: sodium tetrahydroborate / methanol; dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere

3.2: 0 - 5 °C / Inert atmosphere

With sodium tetrahydroborate; oxalyl dichloride; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo2018763

Reference yield:

: 21085-72-3
1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

: 1349833-42-6
methyl (2S,3S,4S,5R,6S)-3,4,5-triacetoxy-6-(4-((4-formylphenylcarbamoyloxy)methyl)phenoxy)-tetrahydro-2H-pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: silver(l) oxide / acetonitrile / 18 h / 25 °C / Inert atmosphere; Darkness

2.1: sodium tetrahydroborate / methanol; dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 0 - 25 °C / Inert atmosphere

3.2: 0 - 5 °C / Inert atmosphere

With sodium tetrahydroborate; oxalyl dichloride; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo2018763