N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide

Base Information

Chemical Name:N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide
CAS No.:791608-07-6
Molecular Formula:C₂₂H₂₈N₂O₄
Molecular Weight:384.475
Hs Code.:

Synonyms:N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide

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Chemical Property of N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide

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Technology Process of N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide

There total 9 articles about N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide 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: 63.0%

: 791608-05-4
N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide

: 791608-07-6
N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide

Guidance literature:: N-(7,8-bis-benzyloxy-3-oxo-hexahydro-oxazolo[3,4-a]pyridin-6-yl)-N-(4-methoxy-benzyl)-acetamide; With ammonium cerium(IV) nitrate; In water; acetonitrile; at 20 ℃;

With barium dihydroxide; In ethanol; water; Heating;
DOI:10.1002/anie.200453863

Reference yield:

: 791608-14-5
Benzoic acid (S)-1-((R)-3-allyl-2-oxo-oxazolidin-4-yl)-allyl ester

: 791608-07-6
N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / Grubbs catalyst / toluene / 20 °C

2.1: 85 percent / K₂CO₃ / methanol / 20 °C

3.1: 91 percent / NaH / dimethylformamide / 0 - 20 °C

4.1: 90 percent / (DHQD)2Phal; K₂CO₃; CH₃SO₂NH₂ / K₃[Fe(CN)6]; K₂OsO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

5.1: nBu₂SnO / toluene / Heating

5.2: 69 percent / Bu₄NBr / toluene / 100 °C

6.1: 86 percent / (COCl)2; DMSO; N,N-diisopropylethylamine / CH₂Cl₂ / -70 - 20 °C

7.1: 78 percent / AcOH; Na(OAc)3BH / 1,2-dichloro-ethane / 20 °C

8.1: 86 percent / pyridine; 4-dimethylaminopyridine / 0 - 20 °C

9.1: ceric ammonium nitrate / acetonitrile; H₂O / 20 °C

9.2: 63 percent / Ba(OH)2*8H₂O / ethanol; H₂O / Heating

With pyridine; dmap; oxalyl dichloride; ammonium cerium(IV) nitrate; methanesulfonamide; sodium tris(acetoxy)borohydride; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; potassium osmate(VI); Grubbs catalyst first generation; potassium hexacyanoferrate(III); In methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 6.1: Swern oxidation;
DOI:10.1002/anie.200453863

Reference yield:

: 241491-22-5
(8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one

: 791608-07-6
N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-hydroxymethyl-piperidin-3-yl)-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: 91 percent / NaH / dimethylformamide / 0 - 20 °C

2.1: 90 percent / (DHQD)2Phal; K₂CO₃; CH₃SO₂NH₂ / K₃[Fe(CN)6]; K₂OsO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

3.1: nBu₂SnO / toluene / Heating

3.2: 69 percent / Bu₄NBr / toluene / 100 °C

4.1: 86 percent / (COCl)2; DMSO; N,N-diisopropylethylamine / CH₂Cl₂ / -70 - 20 °C

5.1: 78 percent / AcOH; Na(OAc)3BH / 1,2-dichloro-ethane / 20 °C

6.1: 86 percent / pyridine; 4-dimethylaminopyridine / 0 - 20 °C

7.1: ceric ammonium nitrate / acetonitrile; H₂O / 20 °C

7.2: 63 percent / Ba(OH)2*8H₂O / ethanol; H₂O / Heating

With pyridine; dmap; oxalyl dichloride; ammonium cerium(IV) nitrate; methanesulfonamide; sodium tris(acetoxy)borohydride; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; N-ethyl-N,N-diisopropylamine; potassium osmate(VI); potassium hexacyanoferrate(III); In dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 4.1: Swern oxidation;
DOI:10.1002/anie.200453863