(E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester
• CAS No.: 827026-14-2
• Molecular Formula: C₅₇H₅₉N₃O₁₁
• Molecular Weight: 962.109
• Mol file: 827026-14-2.mol

Synonyms:(E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

Chemical Property of (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester

There total 6 articles about (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic 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:

6'-azido-2,2',3,3',4,4'-hexa-O-benzyl-6'-deoxy-α-D-trehalose (827026-13-1) → (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester (827026-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethylsulfoxide; oxalyl chloride; diisopropylethylamine / CH₂Cl₂ / -65 - 0 °C

2.1: sodium hydride / tetrahydrofuran / 1 h

2.2: 0.16 g / tetrahydrofuran / 12 h

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

6-azido-2,2',3,3',4,4',6'-hepta-O-benzyl-6-deoxy-α,α'-trehalose (827026-12-0) → (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester (827026-14-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic anhydride; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 9 h / -78 - 20 °C

1.2: 50 percent / sodium methoxide / methanol; CH₂Cl₂ / 0.5 h / 20 °C

2.1: dimethylsulfoxide; oxalyl chloride; diisopropylethylamine / CH₂Cl₂ / -65 - 0 °C

3.1: sodium hydride / tetrahydrofuran / 1 h

3.2: 0.16 g / tetrahydrofuran / 12 h

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; acetic anhydride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

Toluene-4-sulfonic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester → (E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-acrylic acid methyl ester (827026-14-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 0.46 g / sodium azide / dimethylformamide / 5 h / 100 °C

2.1: acetic anhydride; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 9 h / -78 - 20 °C

2.2: 50 percent / sodium methoxide / methanol; CH₂Cl₂ / 0.5 h / 20 °C

3.1: dimethylsulfoxide; oxalyl chloride; diisopropylethylamine / CH₂Cl₂ / -65 - 0 °C

4.1: sodium hydride / tetrahydrofuran / 1 h

4.2: 0.16 g / tetrahydrofuran / 12 h

With sodium azide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; acetic anhydride; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation;

DOI:10.1016/j.bmc.2004.09.033

upstream raw materials:

Methyl diethylphosphonoacetate

6'-azido-2,2',3,3',4,4'-hexa-O-benzyl-6'-deoxy-α-D-trehalose

6-azido-2,2',3,3',4,4',6'-hepta-O-benzyl-6-deoxy-α,α'-trehalose

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl-(1?1)-2,3,4,6-tetra-O-benzyl-D-glucopyranoside

Downstream raw materials:

(E)-3-[(2R,3R,4S,5R,6R)-6-((2R,3R,4S,5R,6R)-6-Azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-N-octyl-acrylamide