(2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1426924-91-5
• Molecular Formula: C₂₈H₃₂ClNO₁₀
• Molecular Weight: 578.016
• Mol file: 1426924-91-5.mol

Synonyms:(2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 10 articles about (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-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: 66.5%

(2S,35,4R,5S,6S)-2-(4-chloro-3-(4-(2-oxoethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (1426924-90-4) + N-methoxylamine hydrochloride (593-56-6) → (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (1426924-91-5)

Guidance literature:

With pyridine; sodium acetate; In ethanol; for 5h; Inert atmosphere; Reflux;

Reference yield:

[4-(5-bromo-2-chloro-benzyl)-phenoxy]-tert-butyl-dimethyl-silane (864070-19-9) → (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (1426924-91-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 18 h / -78 - 20 °C

2.1: water; acetic acid / 22 h / 110 °C

2.2: 16 h / 20 °C

3.1: acetic acid; hydrogen bromide / water; dichloromethane / 2.5 h / 20 °C

4.1: zinc(II) oxide / 1 h / 60 °C

5.1: caesium carbonate / N,N-dimethyl-formamide / 36 h / 20 °C

6.1: acetic acid / tetrahydrofuran; water / 24 h / 0 - 20 °C

7.1: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.08 h / -78 °C / Inert atmosphere

8.1: pyridine; sodium acetate / ethanol / 5 h / Inert atmosphere; Reflux

With pyridine; n-butyllithium; oxalyl dichloride; hydrogen bromide; sodium acetate; caesium carbonate; acetic acid; zinc(II) oxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

(3S,4R,5S,6S)-6-(3-(4-acetoxybenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (1309963-55-0) → (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-(methoxyimino)ethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (1426924-91-5)

Guidance literature:

Multi-step reaction with 6 steps

1: acetic acid; hydrogen bromide / water; dichloromethane / 2.5 h / 20 °C

2: zinc(II) oxide / 1 h / 60 °C

3: caesium carbonate / N,N-dimethyl-formamide / 36 h / 20 °C

4: acetic acid / tetrahydrofuran; water / 24 h / 0 - 20 °C

5: oxalyl dichloride / dichloromethane; dimethyl sulfoxide / 2.08 h / -78 °C / Inert atmosphere

6: pyridine; sodium acetate / ethanol / 5 h / Inert atmosphere; Reflux

With pyridine; oxalyl dichloride; hydrogen bromide; sodium acetate; caesium carbonate; acetic acid; zinc(II) oxide; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

[4-(5-bromo-2-chloro-benzyl)-phenoxy]-tert-butyl-dimethyl-silane

(2S,35,4R,5S,6S)-2-(4-chloro-3-(4-(2-oxoethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

N-methoxylamine hydrochloride

(3aS,5R,6R,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

Downstream raw materials:

2-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenoxy)acetaldehyde O-methyl oxime