(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1309964-02-0
• Molecular Formula: C₃₅H₄₇ClO₁₁Si
• Molecular Weight: 707.29

Synonyms:(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 6 articles about (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)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: 60.85%

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1079083-63-8) + 2-(tert-butyldimethylsilyloxy)ethyl bromide (86864-60-0) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1309964-02-0)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 36h;

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6,55515-28-1,55515-29-2,32384-65-9) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1309964-02-0)

Guidance literature:

Multi-step reaction with 4 steps

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

1.2: 4 h / -78 °C

1.3: 16 h / -78 - 20 °C

2.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: triethylsilane; boron trifluoride diethyl etherate; water / acetonitrile / 22 h / 10 - 30 °C

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

With triethylsilane; dmap; n-butyllithium; boron trifluoride diethyl etherate; water; caesium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile; pentane;

Reference yield:

(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-chlorophenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (1309963-64-1) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(2-((tert-butyldimethylsilyl)oxy)ethoxy)benzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1309964-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylsilane; boron trifluoride diethyl etherate; water / acetonitrile / 22 h / 10 - 30 °C

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

With triethylsilane; boron trifluoride diethyl etherate; water; caesium carbonate; In N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4S,5S,6R)-2-(3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

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

(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-chlorophenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

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

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

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

(2R,3R,4R,5S,65)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-oxoethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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