(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine

Base Information

Chemical Name:(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine
CAS No.:124330-54-7
Molecular Formula:C₇₀H₇₃NO₈
Molecular Weight:1056.35
Hs Code.:

(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine

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Chemical Property of (1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine

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Technology Process of (1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine

There total 8 articles about (1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine 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: 63.0%

: 38665-10-0
(+)-validoxylamine A

: 100-39-0
benzyl bromide

: 124330-54-7
(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; Inert atmosphere;
DOI:10.1021/ja203574u

Reference yield:

: 86756-42-5,102131-10-2
(4aR,6S,7S,8S,8aR)-7,8-bis(benzyloxy)-2-phenyl-N-((1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)cyclohex-2-en-1-yl)hexahydro-4H-benzo[d][1,3]dioxin-6-amine

: 124330-54-7
(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine

Guidance literature:: Multi-step reaction with 2 steps

1: N-bromosuccinimide / dimethylformamide; H₂O / 17 h / Ambient temperature

2: 1) HCl, 2) NaBH₃CN, MgSO₄ / 1) MeOH, 10 min RT, 2) MeOH, 3h, reflux

With hydrogenchloride; N-Bromosuccinimide; sodium cyanoborohydride; magnesium sulfate; In water; N,N-dimethyl-formamide;

Reference yield:

: validoxylamine A 7'-phosphate

: 124330-54-7
(1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine

Guidance literature:: Multi-step reaction with 2 steps

1: recombinant cyclitol nucleotidyltransferase from Streptomyces hygroscopicus subsp. limoneus KCCM 11405; recombinant phosphatase from Streptomyces hygroscopicus subsp. limoneus KCCM 11405; validamine 7-phosphate; valienol 1-phosphate; magnesium chloride / 3 h / 30 °C / pH 7.5 / aq. buffer

2: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere

With recombinant cyclitol nucleotidyltransferase from Streptomyces hygroscopicus subsp. limoneus KCCM 11405; recombinant phosphatase from Streptomyces hygroscopicus subsp. limoneus KCCM 11405; valienol 1-phosphate; validamine 7-phosphate; sodium hydride; magnesium chloride; In N,N-dimethyl-formamide;
DOI:10.1021/ja203574u