4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene

Base Information

• Chemical Name: 4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene
• CAS No.: 239806-28-1
• Molecular Formula: C₂₉H₃₅IO₁₃
• Molecular Weight: 718.494
• Mol file: 239806-28-1.mol

Synonyms:4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene

Chemical Property of 4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene

There total 1 articles about 4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene 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: 67.0%

hexa-O-acetyl-D-maltal (51450-24-9,67314-34-5,67314-36-7,71276-40-9) + 1-bromomethyl-4-iodobenzene (16004-15-2) → 4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene (239806-28-1)

Guidance literature:

1-bromomethyl-4-iodobenzene; With chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; at 0 ℃; for 1.5h;

hexa-O-acetyl-D-maltal; With boron trifluoride diethyl etherate; In dichloromethane; at -30 - 0 ℃; for 0.666667h;

DOI:10.1021/jo990253e

Reference yield:

(R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester (108957-20-6) + 4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene (239806-28-1) → Nα-(tert-butoxycarbonyl)-C-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->4)-(6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)]-L-tyrosine benzyl ester (239806-29-2) + Nα-(tert-butoxycarbonyl)-C-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->4)-(6-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)]-L-tyrosine benzyl ester

Guidance literature:

(R)-N-(tert-butoxycarbonyl)-3-iodoalanine benzyl ester; With chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; at 35 ℃; for 2.5h;

4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene; dichlorobis(tri-O-tolylphosphine)palladium; In tetrahydrofuran; N,N-dimethyl acetamide; at 20 - 55 ℃; for 2.5h;

DOI:10.1021/jo990253e

Reference yield:

4-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->5)-(7-O-acetyl-2,6-anhydro-1,3,4-trideoxy-α,β-D-erythro-hept-3-enitol-1-yl)]iodobenzene (239806-28-1) → (S)-2-tert-Butoxycarbonylamino-3-{4-[(2R,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl]-phenyl}-propionic acid

Guidance literature:

Multi-step reaction with 4 steps

1.1: zinc; 1,2-dibromoethane; TMSCl / tetrahydrofuran / 2.5 h / 35 °C

1.2: 950 mg / bis(tri-o-tolylphosphine)palladium dichloride / N,N-dimethyl-acetamide; tetrahydrofuran / 2.5 h / 20 - 55 °C

2.1: N-methylmorpholine N-oxide / OsO₄ / 2-methyl-propan-2-ol; acetone; H₂O / 24 h / 20 °C

3.1: 252 mg / DMAP; pyridine / 1 h / 0 - 20 °C

4.1: hydrogen / Pd/C / methanol / 0.5 h / 20 °C / 760 Torr

With pyridine; dmap; chloro-trimethyl-silane; hydrogen; 4-methylmorpholine N-oxide; ethylene dibromide; zinc; palladium on activated charcoal; osmium(VIII) oxide; In tetrahydrofuran; methanol; water; acetone; tert-butyl alcohol; 1.1: Metallation / 1.2: Alkylation / 2.1: Oxidation / 3.1: Acetylation / 4.1: Hydrogenolysis;

DOI:10.1021/jo990253e

upstream raw materials:

hexa-O-acetyl-D-maltal

1-bromomethyl-4-iodobenzene

Downstream raw materials:

N^α-(tert-butoxycarbonyl)-C-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->4)-(6-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)]-L-tyrosine benzyl ester

N^α-(tert-butoxycarbonyl)-C-[(2',3',4',6'-tetra-O-acetyl-α-D-glucopyranosyl)-(1'->4)-(2,3,6-tri-O-acetyl-α-D-mannopyranosyl)]-L-tyrosine benzyl ester