N-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyl]isocyanate

Base Information

• Chemical Name: N-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyl]isocyanate
• CAS No.: 190325-99-6
• Molecular Formula: C₃₆H₃₅NO₅
• Molecular Weight: 561.678
• Mol file: 190325-99-6.mol

Synonyms:N-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyl]isocyanate

Chemical Property of N-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyl]isocyanate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyl]isocyanate

There total 2 articles about N-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyl]isocyanate 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: 58.0%

bis(trichloromethyl) carbonate (32315-10-9) + (1R,2S,3S,4R)-1-amino-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-2,3,4-triol (128573-02-4) → N-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyl]isocyanate (190325-99-6)

Guidance literature:

With pyridine; In dichloromethane; at -60 ℃;

DOI:10.1071/C96151

Reference yield:

1D-(1,3/2,6)-6-azido-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene (128573-01-3) → N-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyl]isocyanate (190325-99-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / H₂S gas, pyridine, Et₃N / H₂O / 2 h

2: 58 percent / pyridine / CH₂Cl₂ / -60 °C

With pyridine; hydrogen sulfide; triethylamine; In dichloromethane; water;

DOI:10.1071/C96151

Reference yield: 28.0%

ethanol (64-17-5) + N-[(1R,4R,5S,6S)-4,5,6-tribenzyloxy-3-(benzyloxymethyl)-cyclohex-2-enyl]isocyanate (190325-99-6) → ((1R,4R,5S,6S)-4,5,6-Tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enyl)-carbamic acid ethyl ester

Guidance literature:

In toluene; at 100 ℃;

DOI:10.1071/C96151

upstream raw materials:

bis(trichloromethyl) carbonate

(1R,2S,3S,4R)-1-amino-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-2,3,4-triol

1D-(1,3/2,6)-6-azido-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene

Downstream raw materials:

((1R,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-carbamic acid (2R,3S,4R,5R,6R)-4,5-dihydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester