(2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 87907-05-9
• Molecular Formula: C₃₃H₃₇BrClN₃O₁₃
• Molecular Weight: 799.026
• Mol file: 87907-05-9.mol

Synonyms:(2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 25 articles about (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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: 67.9%

O-(methyl 2,3-di-O-benzyl-4-O-chloroacetyl-β-D-glucopyranosyluronate)-(1->4)-1,3,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranose → (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (87907-05-9)

Guidance literature:

With titanium(IV) bromide; In dichloromethane; ethyl acetate; for 10h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90842-5

Reference yield:

(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-3-(2-chloro-acetoxy)-6-((2R,3S,4R,5R)-4,6-diacetoxy-2-acetoxymethyl-5-azido-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (104530-54-3) → (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (87907-05-9)

Guidance literature:

With titanium(IV) bromide; In dichloromethane; ethyl acetate; at 40 - 45 ℃; for 6h; Inert atmosphere;

Reference yield:

D-Glucose (2280-44-6) → (2S,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-4-Acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yloxy)-4,5-bis-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (87907-05-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: hydrogenchloride / 5 h / 0 - 75 °C / Industry scale

2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 2 h / 100 - 105 °C / Vacuum; Industry scale

3.1: sodium hydroxide / tetrabutylammomium bromide / toluene; 1-methyl-pyrrolidin-2-one / 20 °C / Industry scale

4.1: toluene-4-sulfonic acid; water / methanol / 70 - 75 °C / Industry scale

5.1: pyridine / 80 - 85 °C

5.2: 55 - 60 °C / Industry scale

6.1: water; acetic acid / dichloromethane / 40 - 45 °C / Industry scale

7.1: Jones reagent / acetone / 40 - 45 °C / Industry scale

8.1: potassium tert-butylate / dimethyl sulfoxide / 95 - 122 °C

8.2: pH 2 - 2.5

9.1: potassium carbonate / acetone / 2 h / 30 - 40 °C

10.1: pyridine / dichloromethane / 0 - 10 °C / Industry scale

11.1: water; mercury(II) oxide / water / 20 °C / Industry scale

11.2: Industry scale

12.1: triphenylphosphine; bromine / dichloromethane / 1 h / 20 °C

13.1: mercury dibromide / dichloromethane / 20 °C / Inert atmosphere; Molecular sieve

13.2: 20 °C / Inert atmosphere

14.1: trifluoroacetic acid / 6 h / 20 °C / Inert atmosphere

15.1: titanium(IV) bromide / dichloromethane; ethyl acetate / 6 h / 40 - 45 °C / Inert atmosphere

With pyridine; Jones reagent; potassium tert-butylate; water; bromine; titanium(IV) bromide; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; trifluoroacetic acid; mercury dibromide; mercury(II) oxide; sodium hydroxide; hydrogenchloride; tetrabutylammomium bromide; toluene-4-sulfonic acid; In 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

upstream raw materials:

acetic anhydride

O-(methyl 2,3-di-O-benzyl-4-O-(chloroacetyl)-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

α-D-glucopyranose peracetylate

D-Glucose