N-((1S,2S,3S,4R,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclopentyl)-acetamide

Base Information

• Chemical Name: N-((1S,2S,3S,4R,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclopentyl)-acetamide
• CAS No.: 171877-85-3
• Molecular Formula: C₃₆H₃₉NO₆
• Molecular Weight: 581.709
• Mol file: 171877-85-3.mol

Synonyms:

Chemical Property of N-((1S,2S,3S,4R,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclopentyl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1S,2S,3S,4R,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclopentyl)-acetamide

There total 5 articles about N-((1S,2S,3S,4R,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclopentyl)-acetamide 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:

acetic anhydride (108-24-7) + (2S,3R,4S)-2,3,4,6-Tetrakis-benzyloxy-5-oxo-hexanal O-benzyl-oxime → N-((1S,2S,3S,4R,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclopentyl)-acetamide (171877-85-3)

Guidance literature:

With pyridine; samarium diiodide; water; Yield given. Multistep reaction; 1) THF, -25 deg C, -25 deg C to rt, 2 h; 2) THF, rt, 15 h;

DOI:10.1021/jo970987w

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucopyranoside (59531-24-7) → N-((1S,2S,3S,4R,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclopentyl)-acetamide (171877-85-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / pyridine

2: 79 percent / chromium trioxide-pyridine

3: AIBN, tributyltin hydride

4: LiAlH₄

5: pyridine

With pyridine; lithium aluminium tetrahydride; chromium trioxide pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride;

DOI:10.1016/0040-4039(94)02185-E

Reference yield:

2,3,4,6-tetrakis-O-(phenylmethyl)-D-xylo-hexos-5-ulose 1-(O-methyloxime) (162019-08-1) → N-((1S,2S,3S,4R,5S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclopentyl)-acetamide (171877-85-3)

Guidance literature:

Multi-step reaction with 3 steps

1: AIBN, tributyltin hydride

2: LiAlH₄

3: pyridine

With pyridine; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride;

DOI:10.1016/0040-4039(94)02185-E

upstream raw materials:

acetic anhydride

[1S-(1α,2β,3α,4β,5α)]-2-amino-3,4,5-tris(phenylmethoxy)-1-[(phenylmethoxy)methyl]cyclopentanol

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

2,3,4,6-tetrakis-O-(phenylmethyl)-D-xylo-hexos-5-ulose 1-(O-methyloxime)