(3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine

Base Information

Chemical Name:(3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine
CAS No.:401504-65-2
Molecular Formula:C₄₂H₅₄N₂O₈
Molecular Weight:714.899
Hs Code.:

(3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine

Synonyms:(3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine

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Chemical Property of (3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine

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Technology Process of (3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine

There total 4 articles about (3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine 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: 68.0%

: 309918-23-8
(3R,4S,5R)-N-tert-butyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidene-piperidine-3-carboxylic acid

: (3R,4S,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine hydrochloride

: 401504-65-2
(3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine

Guidance literature:: With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In acetonitrile; at 20 ℃;
DOI:10.1039/b103756k

Reference yield:

: 401504-56-1
(3R,4S,5R)-1-tert-butoxycarbonyl-3,4-dihydroxy-5-(hydroxymethyl)piperidine

: 401504-65-2
(3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 0.17 h / 20 °C

1.2: 48 percent / dimethylformamide / 1 h / 20 °C

2.1: 94 percent / aq. HCl / methanol / 1 h / 20 °C

3.1: 68 percent / Et₃N; HATU / acetonitrile / 20 °C

With hydrogenchloride; sodium hydride; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/b103756k

Reference yield:

: 401504-57-2
(3R,4S,5R)-3,4-bis(benzyloxy)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)piperidine

: 401504-65-2
(3R,4S,5R)-1-[(3R,4S,5R)-1-tert-butoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-bis(benzyloxy)-5-(benzyloxymethyl)piperidine

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / aq. HCl / methanol / 1 h / 20 °C

2: 68 percent / Et₃N; HATU / acetonitrile / 20 °C

With hydrogenchloride; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; acetonitrile;
DOI:10.1039/b103756k