Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine

Base Information

• Chemical Name: Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine
• CAS No.: 819084-35-0
• Molecular Formula: C₃₆H₄₇NO₅
• Molecular Weight: 573.773
• Mol file: 819084-35-0.mol

Synonyms:

Chemical Property of Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine

There total 1 articles about Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine 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: 59.0%

n-hexylmagnesium bromide (3761-92-0) + 3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydohexos-5-ulo-2,5-furanose N-benzylimine (302788-34-7) → Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine (819084-35-0)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.bmcl.2004.09.086

Reference yield:

Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine (819084-35-0) → (2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-hexyl-piperidine-3,5-diol

Guidance literature:

Multi-step reaction with 2 steps

1: aq. TFA / 30 h

2: NaBH₃CN; AcOH / methanol / 30 h

With sodium cyanoborohydride; acetic acid; trifluoroacetic acid; In methanol;

DOI:10.1016/j.bmcl.2004.09.086

Reference yield:

Benzyl-[(R)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-heptyl]-amine (819084-35-0) → (2R,3S,4S,5S)-5-((R)-1-Benzylamino-heptyl)-4-benzyloxy-2-benzyloxymethyl-tetrahydro-furan-2,3-diol

Guidance literature:

With trifluoroacetic acid; for 30h;

DOI:10.1016/j.bmcl.2004.09.086

upstream raw materials:

n-hexylmagnesium bromide

3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydohexos-5-ulo-2,5-furanose N-benzylimine