[(2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-(4-oxiranyl-butyl)-1-oxy-piperidin-2-yl]-methanol

Base Information

Chemical Name:[(2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-(4-oxiranyl-butyl)-1-oxy-piperidin-2-yl]-methanol
CAS No.:134784-91-1
Molecular Formula:C₄₀H₄₇NO₆
Molecular Weight:637.816
Hs Code.:

Synonyms:[(2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-(4-oxiranyl-butyl)-1-oxy-piperidin-2-yl]-methanol

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Chemical Property of [(2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-(4-oxiranyl-butyl)-1-oxy-piperidin-2-yl]-methanol

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Technology Process of [(2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-(4-oxiranyl-butyl)-1-oxy-piperidin-2-yl]-methanol

There total 7 articles about [(2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-(4-oxiranyl-butyl)-1-oxy-piperidin-2-yl]-methanol 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: 67.0%

: 134820-80-7
(N-benzyl)-2(R)-hydroxymethyl-3(R),4(R),5(S)-tribenzyloxy-6(S)-(5-hexenyl)-piperidine

: 134784-91-1
(N-benzyl)-2(R)-hydroxymethyl-3(R),4(R),5(S)-tribenzyloxy-6(S)-(5,6-epoxyhexyl)-piperidine N-oxide

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1) 0 deg C, 15 min, 2) RT, overnight;
DOI:10.1016/S0040-4020(01)81779-8

Reference yield: 54.0%

: 134820-80-7
((2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-hex-5-enyl-piperidin-2-yl)-methanol

: 134784-91-1
[(2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-(4-oxiranyl-butyl)-1-oxy-piperidin-2-yl]-methanol

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1) 0 deg C, 15 min, 2) RT, overnight;
DOI:10.1016/S0040-4020(01)81779-8

Reference yield:

: 73111-58-7,130861-06-2,73111-15-6
2,3,4-tri-O-benzyl-5,6-dideoxy-D-xylo-hex-5-enose

: 134784-91-1
[(2R,3R,4R,5S,6R)-1-Benzyl-3,4,5-tris-benzyloxy-6-(4-oxiranyl-butyl)-1-oxy-piperidin-2-yl]-methanol

Guidance literature:: Multi-step reaction with 5 steps

1: 1) Mg / 1) ether, 15 min, 2) ether, 4h, RT

2: 1) oxalyl chloride, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -65 deg C, 15 min, 2) -65 deg C, 5 min

3: 16 percent / NaBH₃CN, ZnBr₂ / tetrahydrofuran; propan-1-ol; H₂O / 72 h / Heating

4: 1) Hg(OTFA)2, 2) O₂, NaBH₄ / 1) THF, 1.75h, 2) DMF, RT, 1h

5: 54 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1) 0 deg C, 15 min, 2) RT, overnight

With sodium tetrahydroborate; oxalyl dichloride; oxygen; mercury(II) trifluoroacetate; sodium cyanoborohydride; magnesium; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; In tetrahydrofuran; propan-1-ol; dichloromethane; water;
DOI:10.1016/S0040-4020(01)81779-8