1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol

Base Information

• Chemical Name: 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol
• CAS No.: 116386-28-8
• Molecular Formula: C₁₉H₂₇NO₆S
• Molecular Weight: 397.492

Synonyms:1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol

Chemical Property of 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol

There total 2 articles about 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol 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: 34.0%

thiophenol (108-98-5) + (1R)-1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1,2-C-methylene-1-nitro-D-mannitol (110085-92-2) → 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol (116386-28-8) + 2-deoxy-3,4:5,6-di-O-isopropylidene-2-C-(phenylthio)methyl-D-mannonothiohydroxymate (116409-57-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; paraffin; for 4h; Heating;

DOI:10.1016/0008-6215(88)85098-5

Reference yield:

(4S,5R,4'R)-2,2,2',2'-Tetramethyl-5-((R)-2-nitro-cyclopropyl)-[4,4']bi[[1,3]dioxolanyl] (110085-92-2,110170-46-2,110170-47-3) + thiophenol (108-98-5) → 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol (116386-28-8)

Guidance literature:

With sodium methylate; Yield given. Multistep reaction; 1.) N,N-dimethylformamide, 0 deg C, 5 min, 2.) 60-70 deg C, 2.5 h;

DOI:10.1016/0008-6215(90)80144-R

Reference yield: 98.0%

1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1-nitro-2-C-(phenylthio)methyl-D-mannitol (116386-28-8) → 1,2-dideoxy-3,4;5,6-di-O-isopropylidene-2-C-nitromethyl-1-C-phenylsulfinyl-D-glucitol (131070-52-5,131103-64-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -10 ℃; for 0.25h;

DOI:10.1016/0008-6215(90)80144-R

upstream raw materials:

(4S,5R,4'R)-2,2,2',2'-Tetramethyl-5-((R)-2-nitro-cyclopropyl)-[4,4']bi[[1,3]dioxolanyl]

thiophenol

(1R)-1,2-dideoxy-3,4:5,6-di-O-isopropylidene-1,2-C-methylene-1-nitro-D-mannitol

Downstream raw materials:

2-C-aminomethyl-2-deoxy-3,4;5,6-di-O-isopropylidene-1-S-phenyl-1-thio-D-glucitol

1-chloro-2-deoxy-3,4;5,6-di-O-isopropylidene-2-C-nitromethyl-1-S-phenyl-1-thio-D-glucitol

1,2-dideoxy-3,4;5,6-di-O-isopropylidene-2-C-nitromethyl-1-C-phenylsulfinyl-D-glucitol

(R)-1-[(4R,5R)-2,2-Dimethyl-5-((R)-1-nitromethyl-2-phenylsulfanyl-ethyl)-[1,3]dioxolan-4-yl]-ethane-1,2-diol

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