(2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol

Base Information

• Chemical Name: (2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol
• CAS No.: 138328-92-4
• Molecular Formula: C₁₈H₂₀N₆O₂
• Molecular Weight: 352.396
• Mol file: 138328-92-4.mol

Synonyms:(2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol

Chemical Property of (2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol

There total 6 articles about (2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol 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:

mannitol (69-65-8) → (2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol (138328-92-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) H₂SO₄, 2.) 70 percent aq. AcOH / 1.) 23 deg C, 24 h, 2.) 40 deg C, 2 h

2: CHCl₃ / 3 h / 23 °C

3: sodium methoxide / tetrahydrofuran / 4 h / 23 °C

4: 82 percent / CuI / tetrahydrofuran / 3 h / -40 to 0 deg C

5: triphenylphosphine, diethyl azodicarboxylate, diphenylphosphoryl azide / toluene / 12 h / 0 to 23 deg C

6: 40 percent aq. acetic acid / 3 h / 90 °C

With copper(l) iodide; sulfuric acid; diphenylphosphoranyl azide; sodium methylate; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; chloroform; toluene;

DOI:10.1016/S0040-4039(00)93541-X

Reference yield:

(2R,3R,4R,5R)-3,4-O-isopropylidene-1,6-diphenyl-2,3,4,5-hexanetetraol (136740-96-0) → (2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol (138328-92-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine, diethyl azodicarboxylate, diphenylphosphoryl azide / toluene / 12 h / 0 to 23 deg C

2: 40 percent aq. acetic acid / 3 h / 90 °C

With diphenylphosphoranyl azide; acetic acid; triphenylphosphine; diethylazodicarboxylate; In toluene;

DOI:10.1016/S0040-4039(00)93541-X

Reference yield:

1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol (63700-05-0) → (2S,3R,4R,5S)-2,5-Diazido-1,6-diphenyl-hexane-3,4-diol (138328-92-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / CuI / tetrahydrofuran / 3 h / -40 to 0 deg C

2: triphenylphosphine, diethyl azodicarboxylate, diphenylphosphoryl azide / toluene / 12 h / 0 to 23 deg C

3: 40 percent aq. acetic acid / 3 h / 90 °C

With copper(l) iodide; diphenylphosphoranyl azide; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4039(00)93541-X

upstream raw materials:

2S,5S-Diazido-1,6-diphenyl-3,4-O-isopropylidenehexane-3R,4R-diol

mannitol

(2R,3R,4R,5R)-3,4-O-isopropylidene-1,6-diphenyl-2,3,4,5-hexanetetraol

1,2;5,6-dianhydro-3,4-O-isopropylidene-D-mannitol

Downstream raw materials:

(2S,3R,4R,5S)-2,5-bis[(1,1-dimethylethoxy)carbonyl]amino-1,6-diphenyl-3,4-dihydroxyhexane

(2S,3R,4R,5S)-2,5-diamino-3,4-dihydroxy-1,6-diphenylhexane

A-75925

(4S,5R,4'S,5'R)-5,5'-bis(4-benzyloxazolidin-2-one)