(1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol

Base Information

• Chemical Name: (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol
• CAS No.: 227930-76-9
• Molecular Formula: C₄₃H₄₃NO₆
• Molecular Weight: 669.818
• Mol file: 227930-76-9.mol

Synonyms:(1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol

Chemical Property of (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol

There total 9 articles about (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol 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: 75.0%

isocyanate de chlorosulfonyle (1189-71-5) + ((1R,2S,3S,4R)-5-(benzyloxymethyl)cyclohex-5-ene-1,2,3,4-tetrayl)tetrakis(oxy)tetrakis(methylene)tetrabenzene → benzyl (1R,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-(benzyloxymethyl)cyclohex-2-enylcarbamate + (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol (227930-76-9)

Guidance literature:

isocyanate de chlorosulfonyle; ((1R,2S,3S,4R)-5-(benzyloxymethyl)cyclohex-5-ene-1,2,3,4-tetrayl)tetrakis(oxy)tetrakis(methylene)tetrabenzene; With sodium carbonate; In toluene; at 0 ℃; for 12h; Inert atmosphere;

With sodium sulfite; In water; ethyl acetate; toluene; at 20 ℃; for 24h; Optical yield = 92.857 %de; diastereoselective reaction;

DOI:10.1016/j.tet.2013.09.098

Reference yield: 70.0%

C36H35NO5 + benzyl alcohol (100-51-6,185532-71-2) → (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol (227930-76-9)

Guidance literature:

In dichloromethane; -20 deg C -> room temp.;

DOI:10.1002/(SICI)1522-2675(19990505)82:5<645::AID-HLCA645>3.0.CO;2-K

Reference yield: 41.0%

(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine (124330-54-7) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl ((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)carbamate (1316231-06-7) + (1L)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-[(benzyloxycarbonyl)amino]-6-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3-triol (227930-76-9)

Guidance literature:

(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine; With N-Bromosuccinimide; In water; acetonitrile; at 20 ℃; for 15h; Inert atmosphere;

benzyl chloroformate; With sodium hydrogencarbonate; In methanol; chloroform; toluene; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ja203574u

upstream raw materials:

benzyl alcohol

1,3,4,5-tetra-O-benzyl-6,7-dideoxy-L-xylo-hept-6-en-2-ulose

(1D)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-C-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3,4-tetrol

(1D)-(1,3,4/2)-1,2,3-tri-O-benzyl-4-C-[(benzyloxy)methyl]cyclohex-5-ene-1,2,3,4-tetrol

Downstream raw materials:

(1L)-(1,3,4/2)-4-acetamido-1,2,3-tri-O-acetyl-4-[(acetoxy)methyl]cyclohex-5-ene-1,2,3-triol

valienamine