4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

Base Information

• Chemical Name: 4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside
• CAS No.: 855270-72-3
• Molecular Formula: C₁₅H₂₃NO₆
• Molecular Weight: 313.351
• Mol file: 855270-72-3.mol

Synonyms:4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

Chemical Property of 4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

There total 3 articles about 4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside 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: 70.0%

4-pentenyl 2-amino-2-N-benxyloxycarbonyl-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside (855270-80-3) → 4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside (855270-72-3) + 4-pentenyl 2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside (855270-99-4)

Guidance literature:

With sodium hydride; In methanol; toluene; at -70 - -15 ℃; for 0.75h;

DOI:10.1021/jo0500129

Reference yield: 47.0%

4-pentenyl 2-amino-2-N-benxyloxycarbonyl-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside (855270-80-3) + methanol (67-56-1) → 4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside (855270-72-3) + 4-pentenyl 2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-3-O-methoxycarbonyl-α-D-mannopyranoside

Guidance literature:

With caesium carbonate; at -15 - 0 ℃;

DOI:10.1021/jo0500129

Reference yield: 34.0%

3-O-carbamoyl-4,6-O-isopropylidene-D-glucal (855270-65-4) + n-Pent-4-enyl alcohol (821-09-0) → 4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-β-D-mannopyranoside (855270-73-4) + 4-pentenyl 2-amino-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside (855270-72-3) + 4,6-O-isopropylidene-1,5-anhydro-2-deoxy-D-erythro-hex-1-en-3-ulose (51450-38-5)

Guidance literature:

With dirhodium tetraacetate; iodosylbenzene; In hexane; benzene; at 23 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/ol900126q

upstream raw materials:

4-pentenyl 2-amino-2-N-benxyloxycarbonyl-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranoside

methanol

3-O-carbamoyl-4,6-O-isopropylidene-D-glucal

n-Pent-4-enyl alcohol

Downstream raw materials:

6-O-(3-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

1-adamantyl 3,4,6-tri-O-acetyl-2-amino-2-N-benzyloxycarbonyl-2-deoxy-α-D-mannopyranoside

6-O-(2-amino-2-N-benzyloxycarbonyl-2-N,3-O-carbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

6-O-(2-amino-2-N-benzyloxycarbonyl-2-deoxy-4,6-O-isopropylidene-α-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside