(2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-triol
• CAS No.: 134820-81-8
• Molecular Formula: C₁₉H₃₀ClNO₅
• Molecular Weight: 387.904
• Mol file: 134820-81-8.mol

Synonyms:(2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-triol

Chemical Property of (2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-triol

There total 6 articles about (2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-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: 98.0%

6-((2R,3S,4R,5R,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-hydroxymethyl-1-oxy-piperidin-2-yl)-2-chloro-hexan-1-ol (134784-89-7) → (2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-triol (134820-81-8)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In ethanol; for 1.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81779-8

Reference yield:

(3R,4S,5S)-3,4,5-tribenzyloxydodeca-1,11-dien-6-ol (134784-86-4,134877-02-4) → (2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-triol (134820-81-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) oxalyl chloride, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -65 deg C, 15 min, 2) -65 deg C, 5 min

2: 16 percent / NaBH₃CN, ZnBr₂ / tetrahydrofuran; propan-1-ol; H₂O / 72 h / Heating

3: 1) Hg(OTFA)2, 2) O₂, NaBH₄ / 1) THF, 1.75h, 2) DMF, RT, 1h

4: 54 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) RT, overnight

5: 98 percent / HCl / CH₂Cl₂ / 0.08 h / 0 °C

6: 98 percent / H₂, methanolic HCl / 10percent Pd-C / ethanol / 1.5 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; oxalyl dichloride; hydrogen; oxygen; mercury(II) trifluoroacetate; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; palladium on activated charcoal; In tetrahydrofuran; propan-1-ol; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4020(01)81779-8

Reference yield:

3,4,5-tris(benzyloxy)-2-(bromomethyl)-6-methoxytetrahydro-2H-pyran (73111-14-5) → (2R,3S,4R,5R,6R)-1-Benzyl-2-(5-chloro-6-hydroxy-hexyl)-6-hydroxymethyl-piperidine-3,4,5-triol (134820-81-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) Zn, CeCl₃*7H₂O, 2) p-TsOH / 1) MeOH, 3h, reflux, 2) acetone, 1.5h, RT

2: 1) Mg / 1) ether, 15 min, 2) ether, 4h, RT

3: 1) oxalyl chloride, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -65 deg C, 15 min, 2) -65 deg C, 5 min

4: 16 percent / NaBH₃CN, ZnBr₂ / tetrahydrofuran; propan-1-ol; H₂O / 72 h / Heating

5: 1) Hg(OTFA)2, 2) O₂, NaBH₄ / 1) THF, 1.75h, 2) DMF, RT, 1h

6: 54 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) RT, overnight

7: 98 percent / HCl / CH₂Cl₂ / 0.08 h / 0 °C

8: 98 percent / H₂, methanolic HCl / 10percent Pd-C / ethanol / 1.5 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; hydrogen; oxygen; mercury(II) trifluoroacetate; sodium cyanoborohydride; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; zinc; palladium on activated charcoal; In tetrahydrofuran; propan-1-ol; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4020(01)81779-8

upstream raw materials:

6-((2R,3S,4R,5R,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-hydroxymethyl-1-oxy-piperidin-2-yl)-2-chloro-hexan-1-ol

3,4,5-tris(benzyloxy)-2-(bromomethyl)-6-methoxytetrahydro-2H-pyran

(3R,4S,5S)-3,4,5-tribenzyloxydodeca-1,11-dien-6-ol

(3R,4S,5S,6R)-6-amino-(N-benzyl)-3,4,5-tribenzyloxydodeca-1,11-diene