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

Base Information

• Chemical Name: 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
• CAS No.: 827026-10-8
• Molecular Formula: C₇₄H₉₀N₄O₁₃
• Molecular Weight: 1243.55
• Mol file: 827026-10-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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: 41.0%

(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-carboxy-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid (827026-09-5) + caprylic hydrazide (6304-39-8) → 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 (827026-10-8)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

C54H54O11 (897365-18-3) → 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 (827026-10-8)

Guidance literature:

Multi-step reaction with 5 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

5.1: 41 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 20 °C

With lithium hydroxide; sodium chlorite; sodium dihydrogen phosphate; oxalyl dichloride; dihydrogen peroxide; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.bmc.2004.09.033

Reference yield:

C54H52Cl2O11 → 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 (827026-10-8)

Guidance literature:

Multi-step reaction with 3 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

3.1: 41 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / dimethylformamide / 20 °C

With lithium hydroxide; sodium hydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

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

caprylic hydrazide

C₅₄H₅₄O₁₁

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

Refernces