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

Base Information

Chemical Name:(1S,2S,3R,4R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methoxymethylene-1,3,4-cyclohexanetriol
CAS No.:106265-19-4
Molecular Formula:C₃₀H₃₁NO₅
Molecular Weight:485.58
Hs Code.:

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

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

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

There total 12 articles about (1S,2S,3R,4R)-3,4-di-O-benzyl-2-benzylamino-1,2-N,O-carbonyl-5-methoxymethylene-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: 74.0%

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

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 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

Guidance literature:: (methoxymethyl)triphenylphosphonium chloride; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.166667h;

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

2L-(2,4,5/3) 2,3-di-O-benzyloxy-4-N-benzyl-4-N-benzyloxycarbonyl-amino-5-hydroxy-cyclohexanone; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Solvent;
DOI:10.1002/ejoc.202001203

Reference yield: 60.0%

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 106265-18-3,121843-63-8
benzyl benzyl((2R,3S)-2,3-bis(benzyloxy)-6-hydroxy-4-oxocyclohexyl)carbamate

: 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

Guidance literature:: With n-butyllithium; In 1,2-dimethoxyethane; at 0 - 10 ℃;
DOI:10.1016/0040-4039(92)80009-9

Reference yield:

: 4,6-O-benzylidene-2-N-benzyloxycarbonylamino-2-deoxy-D-glucopyranoside

: 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

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 0 - 23 °C

2.1: acetic acid / water / 3 h / 90 °C

3.1: triphenylphosphine; 1H-imidazole; iodine / toluene / 3 h / 60 - 80 °C

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 23 °C

5.1: sulfuric acid; mercury(II) sulfate / water; 1,4-dioxane / 3 h / 80 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 - 0 °C

6.2: 1 h / 0 °C

6.3: 2 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; sulfuric acid; iodine; sodium hydride; mercury(II) sulfate; acetic acid; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; hexane; water; N,N-dimethyl-formamide; toluene; mineral oil; 5.1: |Ferrier Carbohydrate Rearrangement / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination;
DOI:10.1002/ejoc.202001203