[(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate
• CAS No.: 1291094-43-3
• Molecular Formula: C₃₁H₃₄ClNO₁₁
• Molecular Weight: 632.064
• Mol file: 1291094-43-3.mol

Synonyms:[(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate

Chemical Property of [(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate

There total 5 articles about [(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate 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:

2-{4-[2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-benzyl]-2-nitro-phenoxy}-2-methyl-propionic acid ethyl ester (1291094-42-2) → [(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate (1291094-43-3)

Guidance literature:

With iron; acetic acid; at 60 ℃;

Reference yield:

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (461432-25-7) → [(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate (1291094-43-3)

Guidance literature:

Multi-step reaction with 5 steps

1: boron tribromide / dichloromethane / 2.5 h / -78 - -30 °C

2: sodium hydrogencarbonate; water / dichloromethane / 2.5 h / -78 - -30 °C

3: nitric acid; tetrabutylammomium bromide / 1,1-dichloroethane; water / 4 h / 0 - 20 °C

4: caesium carbonate / acetonitrile / 30 h / Inert atmosphere; Reflux

5: acetic acid; iron / 60 °C

With tetrabutylammomium bromide; water; nitric acid; boron tribromide; iron; sodium hydrogencarbonate; caesium carbonate; acetic acid; In 1,1-dichloroethane; dichloromethane; water; acetonitrile;

Reference yield:

(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) → [(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-[(2,2-dimethyl-3-oxo-2H-1,4-benzoxazin-6-yl)methyl]phenyl]tetrahydropyran-2-yl]methyl acetate (1291094-43-3)

Guidance literature:

Multi-step reaction with 3 steps

1: nitric acid; tetrabutylammomium bromide / 1,1-dichloroethane; water / 4 h / 0 - 20 °C

2: caesium carbonate / acetonitrile / 30 h / Inert atmosphere; Reflux

3: acetic acid; iron / 60 °C

With tetrabutylammomium bromide; nitric acid; iron; caesium carbonate; acetic acid; In 1,1-dichloroethane; water; acetonitrile;

upstream raw materials:

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

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

acetic acid (2R,3R,4R,SS,6S)-3,4,5-triacetoxy-6-[4-chloro-3-{4-hydroxy-3-nitro-benzyl}-phenyl]-tetrahydro-pyran-2-ylmethyl ester

2-{4-[2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-benzyl]-2-nitro-phenoxy}-2-methyl-propionic acid ethyl ester

Downstream raw materials:

6-[2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-benzyl]-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one