(3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1416165-10-0
• Molecular Formula: C₂₄H₂₄BrClO₈
• Molecular Weight: 555.807
• Mol file: 1416165-10-0.mol

Synonyms:(3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 5 articles about (3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)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: 90.0%

(3S,4R,5S,6S)-6-(3-(4-acetoxybenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (1309963-55-0) → (3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1416165-10-0)

Guidance literature:

With hydrogen bromide; acetic acid; at 20 ℃; for 1h;

Reference yield:

[4-(5-bromo-2-chloro-benzyl)-phenoxy]-tert-butyl-dimethyl-silane (864070-19-9) → (3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1416165-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 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: hydrogen bromide; acetic acid / 1 h / 20 °C

With n-butyllithium; water; hydrogen bromide; acetic acid; In tetrahydrofuran; hexane;

Reference yield:

(3aS,5R,6R,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde (1018898-77-5) → (3S,4R,5S,6S)-2-bromo-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1416165-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 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: hydrogen bromide; acetic acid / 1 h / 20 °C

With n-butyllithium; water; hydrogen bromide; acetic acid; In tetrahydrofuran; hexane;

upstream raw materials:

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

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

(3S,4R,5S,6S)-6-(3-(4-acetoxybenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Downstream raw materials:

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

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

(2S,3S,4R,5S,6S)-2-(3-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)benzyl)-4-chlorophenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

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