(3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one

Base Information

• Chemical Name: (3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one
• CAS No.: 158349-26-9
• Molecular Formula: C₃₄H₃₅NO₅
• Molecular Weight: 537.656
• Mol file: 158349-26-9.mol

Synonyms:(3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one

Chemical Property of (3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one

There total 4 articles about (3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one 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:

(3S,4S,5S)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-6-hydroxy-piperidin-2-one → (3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (158349-26-9) + (3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-<(benzyloxy)methyl>piperidin-2-one (158349-24-7)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; acetonitrile; at 0 ℃; for 1.5h;

DOI:10.1016/j.tet.2014.01.039

Reference yield:

2,3,4,6-tetra-O-benzyl-D-mannopyranose (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5) → (3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (158349-26-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / dimethyl sulfoxide, acetic anhydride / 12 h

2: 100 percent / 8 N ammonia / methanol / 1.5 h

3: 92 percent / dimethyl sulfoxide, acetic anhydride / 12 h

4: 32 percent / sodium cyanoborohydride / acetonitrile; formic acid / 2 h / Ambient temperature

With ammonium hydroxide; acetic anhydride; sodium cyanoborohydride; dimethyl sulfoxide; In methanol; formic acid; acetonitrile;

DOI:10.1016/S0040-4020(01)86715-6

Reference yield:

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone (82598-88-7) → (3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)piperidin-2-one (158349-26-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / 8 N ammonia / methanol / 1.5 h

2: 92 percent / dimethyl sulfoxide, acetic anhydride / 12 h

3: 32 percent / sodium cyanoborohydride / acetonitrile; formic acid / 2 h / Ambient temperature

With ammonium hydroxide; acetic anhydride; sodium cyanoborohydride; dimethyl sulfoxide; In methanol; formic acid; acetonitrile;

DOI:10.1016/S0040-4020(01)86715-6

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-mannopyranose

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone

2,3,4,6-tetra-O-benzyl-D-mannonamide

Downstream raw materials:

(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one