4-O-acetyl-3-O-benzyl-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-2,6-dideoxy-6-iodo-α-D-glucopyranoside

Base Information

• Chemical Name: 4-O-acetyl-3-O-benzyl-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-2,6-dideoxy-6-iodo-α-D-glucopyranoside
• CAS No.: 117300-09-1
• Molecular Formula: C₃₃H₃₇IO₇
• Molecular Weight: 672.557

Synonyms:4-O-acetyl-3-O-benzyl-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-2,6-dideoxy-6-iodo-α-D-glucopyranoside

Chemical Property of 4-O-acetyl-3-O-benzyl-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-2,6-dideoxy-6-iodo-α-D-glucopyranoside

Chemical Property:

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Technology Process of 4-O-acetyl-3-O-benzyl-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-2,6-dideoxy-6-iodo-α-D-glucopyranoside

There total 2 articles about 4-O-acetyl-3-O-benzyl-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-2,6-dideoxy-6-iodo-α-D-glucopyranoside 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:

3-O-benzyl-2-deoxy-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-α-D-glucopyranoside (110046-71-4) → 4-O-acetyl-3-O-benzyl-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-2,6-dideoxy-6-iodo-α-D-glucopyranoside (117300-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine, iodine, imidazole / benzene / 0.5 h / Ambient temperature

2: 4-dimethylaminopyridine / ethyl acetate / Ambient temperature

With 1H-imidazole; dmap; iodine; triphenylphosphine; In ethyl acetate; benzene;

DOI:10.1016/0008-6215(88)85084-5

Reference yield:

acetic anhydride (108-24-7) + (2S,3S,4R,4aS,5S,6S,8aS)-4,5,6-Tris-benzyloxy-2-iodomethyl-6-methyl-hexahydro-pyrano[2,3-b]pyran-3-ol → 4-O-acetyl-3-O-benzyl-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-2,6-dideoxy-6-iodo-α-D-glucopyranoside (117300-09-1)

Guidance literature:

With dmap; In ethyl acetate; Yield given; Ambient temperature;

DOI:10.1016/0008-6215(88)85084-5

Reference yield: 95.0%

4-O-acetyl-3-O-benzyl-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-2,6-dideoxy-6-iodo-α-D-glucopyranoside (117300-09-1) → 2-C-(D-threo-2'-acetoxy-1'-benzyloxy-but-3'-enyl)-3,4-di-O-benzyl-2-deoxy-4-C-methyl-L-xylopyranose

Guidance literature:

With ammonium chloride; zinc; In ethanol; for 0.5h; Heating;

DOI:10.1016/0008-6215(88)85084-5

upstream raw materials:

acetic anhydride

3-O-benzyl-2-deoxy-2-C-(L-threo-1',2'-dibenzyloxy-2'-methylpropane-1',3'-diyl)-α-D-glucopyranoside

Downstream raw materials:

(2S,3S,4S,5R,6R)-2,3,5-Tris-benzyloxy-2,4-dimethyl-octane-1,6-diol

1,4-anhydro-3-O-benzyl-2-C-(D-threo-1'-benzyloxy-2'-methoxymethoxybutyl)-2-deoxy-5-O-methoxymethyl-4-C-methyl-L-xylitol

1,4-anhydro-3-O-benzyl-2,5,6-trideoxy-2-C-(L-erythro-1',2'-dibenzyloxy-3'-methoxymethoxy-2'-methylpropyl)-D-xylitol

(2S,3R,4R)-3-Benzyloxy-2-((1S,2S)-1,2-bis-benzyloxy-3-hydroxy-2-methyl-propyl)-4-hydroxy-hexanoic acid dimethylamide

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