N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-6-hydroxymethyl-piperidin-3-yl)-acetamide

Base Information

• Chemical Name: N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-6-hydroxymethyl-piperidin-3-yl)-acetamide
• CAS No.: 791608-09-8
• Molecular Formula: C₂₆H₃₆N₂O₄
• Molecular Weight: 440.583
• Mol file: 791608-09-8.mol

Synonyms:N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-6-hydroxymethyl-piperidin-3-yl)-acetamide

Chemical Property of N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-6-hydroxymethyl-piperidin-3-yl)-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-6-hydroxymethyl-piperidin-3-yl)-acetamide

There total 9 articles about N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-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:

Benzoic acid (S)-1-((R)-3-allyl-2-oxo-oxazolidin-4-yl)-allyl ester (791608-14-5) → N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-6-hydroxymethyl-piperidin-3-yl)-acetamide (791608-09-8)

Guidance literature:

Multi-step reaction with 10 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

10.1: 95 percent / AcOH; Na(OAc)3BH / 1,2-dichloro-ethane / 20 °C

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:

(8S,8aR)-8-benzyloxy-1,5,8,8a-tetrahydrooxazolo[3,4-a]pyridin-3-one (241491-23-6) → N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-6-hydroxymethyl-piperidin-3-yl)-acetamide (791608-09-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / (DHQD)2Phal; K₂CO₃; CH₃SO₂NH₂ / K₃[Fe(CN)6]; K₂OsO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

2.1: nBu₂SnO / toluene / Heating

2.2: 69 percent / Bu₄NBr / toluene / 100 °C

3.1: 86 percent / (COCl)2; DMSO; N,N-diisopropylethylamine / CH₂Cl₂ / -70 - 20 °C

4.1: 78 percent / AcOH; Na(OAc)3BH / 1,2-dichloro-ethane / 20 °C

5.1: 86 percent / pyridine; 4-dimethylaminopyridine / 0 - 20 °C

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

6.2: 63 percent / Ba(OH)2*8H₂O / ethanol; H₂O / Heating

7.1: 95 percent / AcOH; Na(OAc)3BH / 1,2-dichloro-ethane / 20 °C

With pyridine; dmap; oxalyl dichloride; ammonium cerium(IV) nitrate; methanesulfonamide; sodium tris(acetoxy)borohydride; 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; toluene; acetonitrile; tert-butyl alcohol; 3.1: Swern oxidation;

DOI:10.1002/anie.200453863

Reference yield:

(8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one (241491-22-5) → N-((3R,4R,5R,6R)-4,5-Bis-benzyloxy-1-butyl-6-hydroxymethyl-piperidin-3-yl)-acetamide (791608-09-8)

Guidance literature:

Multi-step reaction with 8 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

8.1: 95 percent / AcOH; Na(OAc)3BH / 1,2-dichloro-ethane / 20 °C

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

upstream raw materials:

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

(6R,7R,8R,8aR)-7,8-Bis-benzyloxy-6-hydroxy-hexahydro-oxazolo[3,4-a]pyridin-3-one

(7S,8R,8aR)-7,8-Bis-benzyloxy-tetrahydro-oxazolo[3,4-a]pyridine-3,6-dione

(6R,7R,8R,8aR)-7,8-Bis-benzyloxy-6-(4-methoxy-benzylamino)-hexahydro-oxazolo[3,4-a]pyridin-3-one