(2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine

Base Information

• Chemical Name: (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine
• CAS No.: 182124-68-1
• Molecular Formula: C₄₁H₅₃NO₅Si
• Molecular Weight: 667.961

Synonyms:(2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine

Chemical Property of (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine

Chemical Property:

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Technology Process of (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine

There total 2 articles about (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine 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:

(3R,4S,5S)-1,3,4,5-Tetrakis-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-heptane-2,6-dione (182124-67-0) → (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine (182124-68-1)

Guidance literature:

With ammonium formate; sodium cyanoborohydride; In methanol; Yield given; Ambient temperature;

DOI:10.1021/jo960362i

Reference yield:

(3S,4S,5R,6R)-1,3,4,5-Tetrakis-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-heptane-2,6-diol → (2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine (182124-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (CF₃CO)2O, DMSO / CH₂Cl₂ / 1.5 h / -78 °C

2: ammonium formate, NaBH₃CN / methanol / Ambient temperature

With ammonium formate; sodium cyanoborohydride; dimethyl sulfoxide; trifluoroacetic anhydride; In methanol; dichloromethane;

DOI:10.1021/jo960362i

Reference yield: 88.0%

(2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(tert-butyl-dimethyl-silanyloxymethyl)-piperidine (182124-68-1) → 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-D-gulo-heptitol (162428-42-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1021/jo960362i

upstream raw materials:

(3R,4S,5S)-1,3,4,5-Tetrakis-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-heptane-2,6-dione

Downstream raw materials:

3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-D-glycero-D-gulo-heptitol

3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-imino-1-O-(p-toluenesulfonyl)-D-glycero-D-gulo-heptitol

(2R,3R,4S,5S,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethyl)-piperidine

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