(E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime

Base Information

• Chemical Name: (E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime
• CAS No.: 112684-46-5
• Molecular Formula: C₄₁H₄₃NO₆
• Molecular Weight: 645.796

Synonyms:(E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime

Chemical Property of (E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime

Chemical Property:

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Technology Process of (E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime

There total 3 articles about (E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime 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: 84.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + N-benzyloxyamine (622-33-3) → (E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime (112684-46-5)

Guidance literature:

In pyridine; methanol; at 90 ℃; for 3.5h;

DOI:10.1021/ol991252b

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + O-benzylhydoxylamine hydrochloride (2687-43-6) → (E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime (112684-46-5) + (Z)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime

Guidance literature:

With pyridine; In methanol; at 60 ℃; for 15h; Title compound not separated from byproducts.;

DOI:10.1039/b315704k

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + O-benzylhydroxylamine hydrochloride → C41H43NO6 + C41H43NO6 + (E)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime (112684-46-5) + (Z)-(2S,3R,4R,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxyhexanal O-benzyloxime

Guidance literature:

With pyridine; at 20 ℃; for 3h; Overall yield = 80 percent; Overall yield = 199 mg;

DOI:10.1021/acs.joc.9b03247

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

N-benzyloxyamine

O-benzylhydoxylamine hydrochloride

Downstream raw materials:

thiocarbonic acid O-phenyl ester O-(2,3,4-tris-benzyloxy-5-benzyloxyimino-1-benzyloxymethyl-pentyl) ester

O-benzyl-N-[(1R,2S,3S,4R,5S)-2,3,4-tris-benzyloxy-5-benzyloxymethylcyclopentyl]-N-hydroxylamine

O-benzyl-N-[(1R,2S,3S,4R,5R)-2,3,4-tris-benzyloxy-5-benzyloxymethylcyclopentyl]-N-hydroxylamine

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

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