(-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol

Base Information

• Chemical Name: (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol
• CAS No.: 949887-66-5
• Molecular Formula: C₃₄H₃₇NO₅
• Molecular Weight: 539.671
• Mol file: 949887-66-5.mol

Synonyms:(-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol

Chemical Property of (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol

There total 8 articles about (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol 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: 70.0%

(+)-(1S,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol (949887-65-4) → (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol (949887-66-5)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1016/j.carres.2007.04.024

Reference yield:

(+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol (4381-96-8,6216-24-6,25348-63-4,80226-74-0,109526-05-8,123354-99-4,123355-00-0,123355-01-1,129829-60-3,129829-61-4,133319-96-7,143615-78-5,143615-79-6) → (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol (949887-66-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 43 percent / tetrahexylammonium bromide; aq. NaOH; chiral diphosphine C44H40N2O2P2 / [η³-allylPdCl]2 / CH2Cl2 / 30 °C

2.1: 99 percent / NaOMe / methanol / 24 h / 20 °C

3.1: 88 percent / m-CPBA / methanol / 20 °C

4.1: NaH / dimethylformamide / 0.5 h / 30 °C

4.2: 68 percent / dimethylformamide / 30 °C

5.1: 61 percent / LiClO₄; NaN₃ / acetonitrile / 24 h / Heating

6.1: 81 percent / Et₃N / tetrahydrofuran / 26 h / 20 °C

7.1: 68 percent / H₂O / dimethylformamide / 96 h / 140 °C

8.1: 70 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

With sodium hydroxide; lithium aluminium tetrahydride; sodium azide; water; sodium methylate; lithium perchlorate; tetrahexylammonium bromide; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; [η³-allylPdCl]2; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/j.carres.2007.04.024

Reference yield:

(+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol (864948-63-0) → (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol (949887-66-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / Et₃N / tetrahydrofuran / 26 h / 20 °C

2: 68 percent / H₂O / dimethylformamide / 96 h / 140 °C

3: 70 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

With lithium aluminium tetrahydride; water; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2007.04.024

upstream raw materials:

(+)-(1S,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol

(+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol

(+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate

(+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane

Downstream raw materials:

(3aS,4S,5R,6S,7R,7aS)-2-(nonylimino)-octahydrobenzo[d]oxazole-4,5,6,7-tetraol

(3aS,4S,5S,6S,7R,7aS)-4-(benzyloxy)-2-(nonylimino)-octahydrobenzo[d]oxazole-5,6,7-triol

1,3-dinonyl-1-((1R,2S,3R,4R,5S,6S)-2,3,4,5-tetrakis(benzyloxy)-6-hydroxycyclohexyl)thiourea

N-((3aS,4S,5R,6S,7S,7aS)-4,5,6,7-tetrakis(benzyloxy)-hexahydrobenzo[d]oxazol-2(3H)-ylidene)nonan-1-amine