(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
Hs Code.:

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

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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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:: 98% ^*data from raw suppliers

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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%

: 401504-52-7
(3S,4R,5R)-3,4-isopropylidenedioxy-5-methylpiperidine

: 401504-55-0
(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carboxylic acid

: 401504-59-4
(3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine

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:

: 65247-32-7
benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside

: 401504-59-4
(3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine

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:

: 123490-19-7
benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside

: 401504-59-4
(3S,4R,5R)-1-[(3R,4S,5R)-1-benzyloxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5'-O-isopropylidenepiperidine-3-carbonyl]-3,4-isopropylidenedioxy-5-methylpiperidine

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