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

Base Information

• Chemical Name: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 866605-99-4
• Molecular Formula: C₂₁H₂₅ClO₁₀
• Molecular Weight: 472.877
• Mol file: 866605-99-4.mol

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

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

There total 5 articles about (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(hydroxymethyl)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:

C37H43ClO10Si (866605-98-3) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (866605-99-4)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2014.04.036

Reference yield:

(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (866605-96-1) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (866605-99-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C

2: pyridine; dmap / chloroform / 20 °C

3: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

With pyridine; triethylsilane; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1016/j.bmc.2014.04.036

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-(4-chloro-3-(hydroxymethyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (866605-99-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tert.-butyl lithium / tetrahydrofuran / 5 h / -78 °C

1.2: -78 - 20 °C

2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C

3.1: pyridine; dmap / chloroform / 20 °C

4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C

With pyridine; triethylsilane; dmap; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tert.-butyl lithium; acetic acid; In tetrahydrofuran; dichloromethane; chloroform;

DOI:10.1016/j.bmc.2014.04.036

upstream raw materials:

C₃₇H₄₃ClO₁₀Si

(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

(2S,3R,4R,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

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

Downstream raw materials:

C₂₈H₃₀ClN₃O₁₁

2-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

6-chloro-2-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

6-bromo-2-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one