1D-(1,2,4/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methylene-1,3,4-cyclohexanetriol

Base Information

• Chemical Name: 1D-(1,2,4/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methylene-1,3,4-cyclohexanetriol
• CAS No.: 106265-20-7
• Molecular Formula: C₂₉H₂₉NO₄
• Molecular Weight: 455.554
• Mol file: 106265-20-7.mol

Synonyms:

Chemical Property of 1D-(1,2,4/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methylene-1,3,4-cyclohexanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1D-(1,2,4/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methylene-1,3,4-cyclohexanetriol

There total 9 articles about 1D-(1,2,4/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methylene-1,3,4-cyclohexanetriol 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%

2L-(2,4,5/3) 2,3-di-O-benzyloxy-4-N-benzyl-4-N-benzyloxycarbonyl-amino-5-hydroxy-cyclohexanone (106265-18-3) + Methylenetriphenylphosphorane (19493-09-5) → 1D-(1,2,4/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methylene-1,3,4-cyclohexanetriol (106265-20-7)

Guidance literature:

In 1,2-dimethoxyethane; at -5 - 10 ℃; for 0.75h;

DOI:10.1039/c39860001399

Reference yield:

benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate (93000-10-3) → 1D-(1,2,4/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methylene-1,3,4-cyclohexanetriol (106265-20-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / NaH / dimethylformamide / 3 h / Ambient temperature

2: aq. acetic acid / 3 h / Heating

3: 60 percent / Ph₃P, imidazole, I₂ / toluene / 3 h / 80 °C

4: 80 percent / NaH / dimethylformamide / 5 h / Ambient temperature

5: 18.2 g / HgSO₄, aq. H₂SO₄ / dioxane / 3 h / 80 °C

6: n-BuLi / 1) 1,2-dimethoxyethane, -70 - 0 deg C, 2) 0 deg C, 45 min

With 1H-imidazole; n-butyllithium; sulfuric acid; iodine; sodium hydride; mercury(II) sulfate; acetic acid; triphenylphosphine; In 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)97594-5

Reference yield:

methyl 3-O-benzyl-2-(N-benzyl-N-benzyloxycarbonylamino)-2-deoxy-α-D-glucopyranoside (129095-44-9) → 1D-(1,2,4/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methylene-1,3,4-cyclohexanetriol (106265-20-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 60 percent / Ph₃P, imidazole, I₂ / toluene / 3 h / 80 °C

2: 80 percent / NaH / dimethylformamide / 5 h / Ambient temperature

3: 18.2 g / HgSO₄, aq. H₂SO₄ / dioxane / 3 h / 80 °C

4: n-BuLi / 1) 1,2-dimethoxyethane, -70 - 0 deg C, 2) 0 deg C, 45 min

With 1H-imidazole; n-butyllithium; sulfuric acid; iodine; sodium hydride; mercury(II) sulfate; triphenylphosphine; In 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)97594-5

upstream raw materials:

2L-(2,4,5/3) 2,3-di-O-benzyloxy-4-N-benzyl-4-N-benzyloxycarbonyl-amino-5-hydroxy-cyclohexanone

Methyltriphenylphosphonium bromide

Methylenetriphenylphosphorane

benzyl ((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl hexahydropyrano[3,2-d][1,3]dioxin-7-yl)carbamate

Downstream raw materials:

1D-(1,2,4,5/3)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxy-methyl-1,3,4-cyclohexanetriol

1D-(1,2,4,5/3)-2-acetamido-1,3,4,7-tetra-O-acetyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol