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

Base Information

• Chemical Name: (E)-3-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((E)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid methyl ester
• CAS No.: 827025-82-1
• Molecular Formula: C₆₀H₆₂O₁₃
• Molecular Weight: 991.144
• Mol file: 827025-82-1.mol

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

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

There total 4 articles about (E)-3-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((E)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-2-yloxy]-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: 82.0%

C54H52Cl2O11 + Methyl diethylphosphonoacetate (1067-74-9) → (E)-3-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((E)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid methyl ester (827025-82-1)

Guidance literature:

Methyl diethylphosphonoacetate; With sodium hydride; In tetrahydrofuran; for 1h;

C₅₄H₅₂Cl₂O₁₁; In tetrahydrofuran; for 12h;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

C54H54O11 (897365-18-3) → (E)-3-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((E)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid methyl ester (827025-82-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 79 percent / sodium chlorite; hydrogen peroxide; sodium dihydrogen phosphate / H₂O; acetonitrile / 12 h / 0 - 20 °C

2.1: oxalyl chloride / CH₂Cl₂ / 1 h / 20 °C

3.1: sodium hydride / tetrahydrofuran / 1 h

3.2: 82 percent / tetrahydrofuran / 12 h

With sodium chlorite; sodium dihydrogen phosphate; oxalyl dichloride; dihydrogen peroxide; sodium hydride; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalopyranuronic acid (827025-76-3) → (E)-3-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((E)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid methyl ester (827025-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl chloride / CH₂Cl₂ / 1 h / 20 °C

2.1: sodium hydride / tetrahydrofuran / 1 h

2.2: 82 percent / tetrahydrofuran / 12 h

With oxalyl dichloride; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2004.09.033

upstream raw materials:

Methyl diethylphosphonoacetate

C₅₄H₅₄O₁₁

2,2',3,3',4,4'-hexa-O-benzyl-α-D-trehalopyranuronic acid

[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-methanol

Downstream raw materials:

(E)-N-Hexyl-3-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((E)-2-hexylcarbamoyl-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylamide

Octanoic acid N'-[(E)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(E)-3-(N'-octanoyl-hydrazino)-3-oxo-propenyl]-tetrahydro-pyran-2-yloxy}-tetrahydro-pyran-2-yl)-acryloyl]-hydrazide

(E)-N-Butyl-3-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((E)-2-butylcarbamoyl-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylamide

(E)-N-(3-Butoxy-propyl)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(E)-2-(3-butoxy-propylcarbamoyl)-vinyl]-tetrahydro-pyran-2-yloxy}-tetrahydro-pyran-2-yl)-acrylamide