(2S,3R,4S,5R)-4-Benzyloxy-2-methyl-piperidine-3,5-diol

Base Information

• Chemical Name: (2S,3R,4S,5R)-4-Benzyloxy-2-methyl-piperidine-3,5-diol
• CAS No.: 117238-35-4
• Molecular Formula: C₁₃H₁₉NO₃
• Molecular Weight: 237.299
• Mol file: 117238-35-4.mol

Synonyms:

Chemical Property of (2S,3R,4S,5R)-4-Benzyloxy-2-methyl-piperidine-3,5-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R)-4-Benzyloxy-2-methyl-piperidine-3,5-diol

There total 11 articles about (2S,3R,4S,5R)-4-Benzyloxy-2-methyl-piperidine-3,5-diol 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:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → (2S,3R,4S,5R)-4-Benzyloxy-2-methyl-piperidine-3,5-diol (117238-35-4)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium hydride, tetrabutylammonium iodide

2: acetic acid / H₂O

3: 85 percent / pyridine

4: 94 percent / lithium triethylborohydride / tetrahydrofuran

5: 4-(diethylamino)pyridine / pyridine

6: 84 percent / sodium azide / dimethylformamide

7: 1.) trifluoroacetic acid; 2.) bromine, barium carbonate / 1.) water; 2.) aqueous dioxane

8: 1.) trifluoromethanesulphonic anhydride, pyridine; 2.) sodium trifluoro acetate; 3.) methanol-water / 2.) DMF

9: 81 percent / H₂ / 5percent Pd/C / ethyl acetate

10: 1.) 1-borane-dimethyl sulfide; 2.) TFA

With pyridine; methanol; diethyl-pyridin-4-yl-amine; sodium azide; trifluoromethylsulfonic anhydride; dimethylsulfide borane complex; hydrogen; bromine; sodium 2,2,2-trifluoroacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; acetic acid; barium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c39880000483

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (57099-04-4) → (2S,3R,4S,5R)-4-Benzyloxy-2-methyl-piperidine-3,5-diol (117238-35-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / pyridine

2: 94 percent / lithium triethylborohydride / tetrahydrofuran

3: 4-(diethylamino)pyridine / pyridine

4: 84 percent / sodium azide / dimethylformamide

5: 1.) trifluoroacetic acid; 2.) bromine, barium carbonate / 1.) water; 2.) aqueous dioxane

6: 1.) trifluoromethanesulphonic anhydride, pyridine; 2.) sodium trifluoro acetate; 3.) methanol-water / 2.) DMF

7: 81 percent / H₂ / 5percent Pd/C / ethyl acetate

8: 1.) 1-borane-dimethyl sulfide; 2.) TFA

With pyridine; methanol; diethyl-pyridin-4-yl-amine; sodium azide; trifluoromethylsulfonic anhydride; dimethylsulfide borane complex; hydrogen; bromine; sodium 2,2,2-trifluoroacetate; lithium triethylborohydride; barium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c39880000483

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose (22331-21-1) → (2S,3R,4S,5R)-4-Benzyloxy-2-methyl-piperidine-3,5-diol (117238-35-4)

Guidance literature:

Multi-step reaction with 9 steps

1: acetic acid / H₂O

2: 85 percent / pyridine

3: 94 percent / lithium triethylborohydride / tetrahydrofuran

4: 4-(diethylamino)pyridine / pyridine

5: 84 percent / sodium azide / dimethylformamide

6: 1.) trifluoroacetic acid; 2.) bromine, barium carbonate / 1.) water; 2.) aqueous dioxane

7: 1.) trifluoromethanesulphonic anhydride, pyridine; 2.) sodium trifluoro acetate; 3.) methanol-water / 2.) DMF

8: 81 percent / H₂ / 5percent Pd/C / ethyl acetate

9: 1.) 1-borane-dimethyl sulfide; 2.) TFA

With pyridine; methanol; diethyl-pyridin-4-yl-amine; sodium azide; trifluoromethylsulfonic anhydride; dimethylsulfide borane complex; hydrogen; bromine; sodium 2,2,2-trifluoroacetate; lithium triethylborohydride; acetic acid; barium carbonate; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c39880000483

upstream raw materials:

(3S,4R,5R,6S)-4-Benzyloxy-3,5-dihydroxy-6-methyl-piperidin-2-one

(1,2:5,6)-di-O-isopropylidene-D-gulose

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose

Downstream raw materials:

deoxyfuconojirimycin

Refernces