(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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid

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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid
• CAS No.: 827026-09-5
• Molecular Formula: C₅₈H₅₈O₁₃
• Molecular Weight: 963.091
• Mol file: 827026-09-5.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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid

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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid

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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid

There total 5 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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid 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: 36.0%

(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) → (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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid (827026-09-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 48h;

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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid (827026-09-5)

Guidance literature:

Multi-step reaction with 4 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

4.1: 36 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 48 h / 20 °C

With lithium hydroxide; 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:

C54H52Cl2O11 → (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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid (827026-09-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 1 h

1.2: 82 percent / tetrahydrofuran / 12 h

2.1: 36 percent / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 48 h / 20 °C

With lithium hydroxide; sodium hydride; In tetrahydrofuran; water;

DOI:10.1016/j.bmc.2004.09.033

upstream raw materials:

(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

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:

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