(3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine

Base Information

• Chemical Name: (3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine
• CAS No.: 401504-59-4
• Molecular Formula: C₂₇H₃₈N₂O₇
• Molecular Weight: 502.608
• Mol file: 401504-59-4.mol

Synonyms:(3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine

Chemical Property of (3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine

There total 14 articles about (3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine 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: 66.0%

(3S,4R,5R)-3,4-isopropylidenedioxy-5-methylpiperidine (401504-52-7) + (3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carboxylic acid (401504-55-0) → (3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine (401504-59-4)

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:

benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside (65247-32-7) → (3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine (401504-59-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 10.1 g / tetrahydrofuran / 19 h / -78 - 20 °C

2.1: H₂ / Pd/C

3.1: 96 percent / H₂ / 5percent Pd/C / methanol / 18 h / 20 °C / 760.05 Torr

4.1: NaBH₄ / ethanol / 0.5 h / 0 °C

5.1: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

6.1: 81 percent / Heating

7.1: 61 percent / H₂O / (Ph₃P)3RhCl / acetonitrile / 3 h / Heating

8.1: 66 percent / Et₃N; HATU / acetonitrile / 20 °C

With dmap; sodium tetrahydroborate; n-butyllithium; water; hydrogen; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; Wilkinson's catalyst; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.1039/b103756k

Reference yield:

benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside (123490-19-7) → (3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine (401504-59-4)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / Pd/C

2: 96 percent / H₂ / 5percent Pd/C / methanol / 18 h / 20 °C / 760.05 Torr

3: NaBH₄ / ethanol / 0.5 h / 0 °C

4: 98 percent / DMAP; Et₃N / CH₂Cl₂ / 20 °C

5: 81 percent / Heating

6: 61 percent / H₂O / (Ph₃P)3RhCl / acetonitrile / 3 h / Heating

7: 66 percent / Et₃N; HATU / acetonitrile / 20 °C

With dmap; sodium tetrahydroborate; water; hydrogen; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; Wilkinson's catalyst; In methanol; ethanol; dichloromethane; acetonitrile;

DOI:10.1039/b103756k

upstream raw materials:

(3S,4R,5R)-3,4-isopropylidenedioxy-5-methylpiperidine

(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carboxylic acid

benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside

benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside