(1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol

Base Information

Chemical Name:(1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol
CAS No.:106265-22-9
Molecular Formula:C₂₉H₃₁NO₅
Molecular Weight:473.569
Hs Code.:

Synonyms:(1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol

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Chemical Property of (1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol

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Technology Process of (1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol

There total 24 articles about (1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol 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: 42.0%

: 106265-19-4
(1S,2S,3R,4R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methoxymethylene-1,3,4-cyclohexanetriol

: 106265-22-9
(1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol

Guidance literature:: (1S,2S,3R,4R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methoxymethylene-1,3,4-cyclohexanetriol; With mercury(II) diacetate; In water; acetonitrile; at 0 - 23 ℃; for 5h;

With potassium iodide; In water; at 23 ℃; for 0.25h;

With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 16h;
DOI:10.1002/ejoc.202001203

Reference yield:

: 106265-18-3
2L-(2,4,5/3) 2,3-di-O-benzyloxy-4-N-benzyl-4-N-benzyloxycarbonyl-amino-5-hydroxy-cyclohexanone

: 106265-22-9
(1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol

Guidance literature:: Multi-step reaction with 2 steps

1: 60 percent / 1,2-dimethoxy-ethane / 0.75 h / -5 - 10 °C

2: 1.) mercury(II) acetate, 2.) aq. KI, NaBH₄ / 1.) H₂O, CH₃CN

With sodium tetrahydroborate; mercury(II) diacetate; potassium iodide; In 1,2-dimethoxyethane;
DOI:10.1039/c39860001399

Reference yield:

: Benzyl-((2S,3R,4R,5S)-4,5-bis-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl)-carbamic acid phenyl ester

: 106265-22-9
(1S,2S,3R,4R,5R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-C-hydroxymethyl-1,3,4-cyclohexanetriol

Guidance literature:: Multi-step reaction with 3 steps

1: HgSO₄, 5 mM H₂SO₄ / dioxane; H₂O / 2 h / 80 °C

3: 1.) mercury(II) acetate, 2.) NaBH₄ / 1.) acetonitrile, H₂O

With sodium tetrahydroborate; sulfuric acid; mercury(II) diacetate; mercury(II) sulfate; In 1,4-dioxane; water;
DOI:10.1021/jo00277a002