(2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)methanol

Base Information

Chemical Name:(2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)methanol
CAS No.:292074-28-3
Molecular Formula:C₂₇H₃₇NO₇
Molecular Weight:487.593
Hs Code.:

Synonyms:(2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)methanol

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Chemical Property of (2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)methanol

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Technology Process of (2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)methanol

There total 16 articles about (2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)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: 92.0%

: 292074-26-1
(2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-vinylpiperidine

: 292074-28-3
(2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)methanol

Guidance literature:: (2R,3R,4R,5R)-3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-vinylpiperidine; With ozone; In methanol; dichloromethane; at -78 ℃;

With sodium tetrahydroborate; In methanol; dichloromethane; at 20 ℃; for 21h; Further stages.;
DOI:10.1021/ol0060432

Reference yield:

: 69-65-8
mannitol

: 292074-28-3
(2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)methanol

Guidance literature:: Multi-step reaction with 15 steps

1.1: 78 percent / ZnCl₂ / 24 h / 20 °C

2.1: NaH / various solvent(s); tetrahydrofuran / 2 h / 0 °C

2.2: 84 percent / tetrabutylammonium iodide / various solvent(s); tetrahydrofuran / 6 h / 20 °C

3.1: 38 percent / acetic acid; water / 3.5 h / 20 °C

4.1: 79 percent / NaIO₄ / H₂O; diethyl ether / 2.5 h / 20 °C

5.1: NaH / various solvent(s); tetrahydrofuran / 0.75 h / 0 °C

5.2: 89 percent / tetrahydrofuran; various solvent(s) / 3 h / -20 °C

6.1: 94 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -20 °C

7.1: 93 percent / pyridine / tetrahydrofuran / 2.5 h / 20 °C

8.1: 95 percent / aq. HCl / tetrahydrofuran / 5 h / 40 °C

9.1: 89 percent / K₂CO₃ / methanol / 2 h / 0 °C

10.1: 47 percent / NaN₃; NH₄Cl / 15-crown-5 / dimethylformamide / 10 h / 55 °C

11.1: 83 percent / ethyldiisopropylamine / 6.5 h / 20 °C

12.1: 46 percent / triphenylphosphine; water / tetrahydrofuran / 16 h / 20 °C

13.1: 95 percent / triethylamine / CH₂Cl₂ / 4 h / 20 °C

14.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 24 h / 20 °C

15.1: O₃ / CH₂Cl₂; methanol / -78 °C

15.2: 92 percent / NaBH₄ / CH₂Cl₂; methanol / 21 h / 20 °C

With pyridine; hydrogenchloride; sodium periodate; sodium azide; water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; ozone; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc(II) chloride; dichloro bis(acetonitrile) palladium(II); 15-crown-5; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Metallation / 2.2: Addition / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Metallation / 5.2: Horner-Wadsworth-Emmons reaction / 6.1: Reduction / 7.1: Acylation / 8.1: Hydrolysis / 9.1: Cyclization / 10.1: Ring cleavage / 11.1: Substitution / 12.1: Reduction / 13.1: Substitution / 14.1: Cyclization / 15.1: ozonolysis / 15.2: Reduction;
DOI:10.1021/ol0060432

Reference yield:

: 106929-09-3
(2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal

: 292074-28-3
(2R,3R,4S,5R)-(3,4-dibenzyloxy-N-tert-butoxycarbonyl-5-methoxymethyloxy-2-piperidinyl)methanol

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / various solvent(s); tetrahydrofuran / 0.75 h / 0 °C

1.2: 89 percent / tetrahydrofuran; various solvent(s) / 3 h / -20 °C

2.1: 94 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 4 h / -20 °C

3.1: 93 percent / pyridine / tetrahydrofuran / 2.5 h / 20 °C

4.1: 95 percent / aq. HCl / tetrahydrofuran / 5 h / 40 °C

5.1: 89 percent / K₂CO₃ / methanol / 2 h / 0 °C

6.1: 47 percent / NaN₃; NH₄Cl / 15-crown-5 / dimethylformamide / 10 h / 55 °C

7.1: 83 percent / ethyldiisopropylamine / 6.5 h / 20 °C

8.1: 46 percent / triphenylphosphine; water / tetrahydrofuran / 16 h / 20 °C

9.1: 95 percent / triethylamine / CH₂Cl₂ / 4 h / 20 °C

10.1: PdCl₂(CH₃CN)2 / tetrahydrofuran / 24 h / 20 °C

11.1: O₃ / CH₂Cl₂; methanol / -78 °C

11.2: 92 percent / NaBH₄ / CH₂Cl₂; methanol / 21 h / 20 °C

With pyridine; hydrogenchloride; sodium azide; water; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ammonium chloride; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; dichloro bis(acetonitrile) palladium(II); 15-crown-5; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Horner-Wadsworth-Emmons reaction / 2.1: Reduction / 3.1: Acylation / 4.1: Hydrolysis / 5.1: Cyclization / 6.1: Ring cleavage / 7.1: Substitution / 8.1: Reduction / 9.1: Substitution / 10.1: Cyclization / 11.1: ozonolysis / 11.2: Reduction;
DOI:10.1021/ol0060432