4-Cyclohexene-1,2,3-triol,6-amino-,(1S,2S,3S,6S)-(9CI)

Base Information

• Chemical Name: 4-Cyclohexene-1,2,3-triol,6-amino-,(1S,2S,3S,6S)-(9CI)
• CAS No.: 173935-16-5
• Molecular Formula: C6H11NO3
• Molecular Weight: 145.158
• Mol file: 173935-16-5.mol

Synonyms:conduramine E;(1S,2S,3S,6S)-6-Amino-cyclohex-4-ene-1,2,3-triol;(+)-conduramine E-4;Konduramin F;

Chemical Property of 4-Cyclohexene-1,2,3-triol,6-amino-,(1S,2S,3S,6S)-(9CI)

Chemical Property:

• Melting Point: 159 - 162 °C (H2O)
• PSA: 86.71000
• LogP: -1.33350

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Cyclohexene-1,2,3-triol,6-amino-,(1S,2S,3S,6S)-(9CI)

There total 10 articles about 4-Cyclohexene-1,2,3-triol,6-amino-,(1S,2S,3S,6S)-(9CI) 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: 91.0%

(3aR,4S,5S,7aS)-5-amino-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol → (+)-conduramine E-4 (173935-16-5,155239-00-2,155239-06-8,157752-14-2,183182-27-6,313217-51-5)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 60 ℃; for 4h;

DOI:10.1021/ol100840n

Reference yield: 64.0%

1D-(1,2/3,4)-4-(t-butoxycarbonyl)amino-1,2-O-isopropylidene-5-cyclohexene-1,2,3-triol (163072-75-1) → (+)-conduramine E-4 (173935-16-5,155239-00-2,155239-06-8,157752-14-2,183182-27-6,313217-51-5)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 4.3h;

DOI:10.1246/bcsj.71.259

Reference yield:

(1S,4S,5S,6S)-4-azido-5,6-(isopropylidenedioxy)cyclohex-2-enol (1188303-61-8) → (+)-conduramine E-4 (173935-16-5,155239-00-2,155239-06-8,157752-14-2,183182-27-6,313217-51-5)

Guidance literature:

(1S,4S,5S,6S)-4-azido-5,6-(isopropylidenedioxy)cyclohex-2-enol; With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 1h; Inert atmosphere;

With water; acetic acid; In diethyl ether; at 0 - 50 ℃; for 22h;

DOI:10.1021/ol9016194

upstream raw materials:

1D-(1,2/3,4)-4-(t-butoxycarbonyl)amino-1,2-O-isopropylidene-5-cyclohexene-1,2,3-triol

(3aS,5aS,8aS,8bS)-2,2-Dimethyl-5a,6,8a,8b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d]oxazol-7-one

(3aS,5aS,8aS,8bS)-2,2-Dimethyl-6-(toluene-4-sulfonyl)-5a,6,8a,8b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d]oxazol-7-one

(3aR,4S,5S,7aS)-5-azido-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-4-ol

Downstream raw materials:

1,3,6-Tri-O-acetyl-2-O-benzyl-4-desoxy-4-<1D-(1N,2,4/3)-(2,3,4-tri-O-acetyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino>-α-D-glucopyranose

1,3,6-Tri-O-acetyl-2-O-benzyl-4-desoxy-4-<1D-(1N,2,4/3)-(2,3,4-tri-O-acetyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino>-β-D-glucopyranose

3-O-Acetyl-1,6-anhydro-2-O-benzyl-4-desoxy-4-<1D-(1N,2,4/3)-(2,3,4-tri-O-acetyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)-amino>-β-D-glucopyranose