Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate

Base Information

• Chemical Name: Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate
• CAS No.: 120927-57-3
• Molecular Formula: C₂₅H₂₇IO₇
• Molecular Weight: 566.39
• Mol file: 120927-57-3.mol

Synonyms:Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate

Chemical Property of Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate

There total 4 articles about Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate 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%

methanol (67-56-1) + Ethyl 3-O-Benzoyl-4-O-benzyl-1,3,6,7-tetradeoxy-D-arabino-octa-1,6(E)-dieno-1,5-pyranose Uronate (137792-77-9) → Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate (120927-57-3)

Guidance literature:

With N-iodo-succinimide; In acetonitrile; for 6h; Ambient temperature;

DOI:10.1021/jo00028a033

Reference yield:

Benzoic acid (2R,3S,4R)-3-benzyloxy-2-hydroxymethyl-3,4-dihydro-2H-pyran-4-yl ester (120927-56-2) → Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate (120927-57-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium chlorochromate, 4-Angstroem molecular sieves / CH₂Cl₂

2: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

3: 67 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

With N-iodo-succinimide; 4 A molecular sieve; sodium hydride; pyridinium chlorochromate; In dichloromethane; acetonitrile;

DOI:10.1021/jo00028a033

Reference yield:

Benzoic acid (2S,3S,4R)-3-benzyloxy-2-formyl-3,4-dihydro-2H-pyran-4-yl ester → Ethyl (Methyl 3-O-benzoyl-4-O-benzyl-2,6,7-trideoxy-2-iodo-α-D-manno-oct-6(E)-eno-1,5-pyranosid)uronate (120927-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NaH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C

2: 67 percent / N-iodosuccinimide / acetonitrile / 6 h / Ambient temperature

With N-iodo-succinimide; sodium hydride; In acetonitrile;

DOI:10.1021/jo00028a033

upstream raw materials:

methanol

diethoxyphosphoryl-acetic acid ethyl ester

Benzoic acid (2R,3S,4R)-3-benzyloxy-2-hydroxymethyl-3,4-dihydro-2H-pyran-4-yl ester

Ethyl 3-O-Benzoyl-4-O-benzyl-1,3,6,7-tetradeoxy-D-arabino-octa-1,6(E)-dieno-1,5-pyranose Uronate

Downstream raw materials:

Benzoic acid (1S,3S,4R,5R,6R,7S)-6-benzyloxy-7-ethoxycarbonylmethyl-3-methoxy-2-oxa-bicyclo[2.2.1]hept-5-yl ester

Benzoic acid (1S,3S,4R,5R,6R,7R)-6-benzyloxy-7-ethoxycarbonylmethyl-3-methoxy-2-oxa-bicyclo[2.2.1]hept-5-yl ester

Benzoic acid (3aR,4S,5R,6R,6aR)-6-benzyloxy-4-dimethoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Benzoic acid (1R,2R,3R,4S,5S)-2-benzyloxy-5-dimethoxymethyl-4-ethoxycarbonylmethyl-3-hydroxy-cyclopentyl ester