(2S,3R,4S)-1-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidine-3,4-diol

Base Information

Chemical Name:(2S,3R,4S)-1-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidine-3,4-diol
CAS No.:1415099-03-4
Molecular Formula:C₁₈H₂₅NO₆
Molecular Weight:351.4
Hs Code.:

Synonyms:(2S,3R,4S)-1-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidine-3,4-diol

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Chemical Property of (2S,3R,4S)-1-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidine-3,4-diol

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Technology Process of (2S,3R,4S)-1-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidine-3,4-diol

There total 4 articles about (2S,3R,4S)-1-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidine-3,4-diol 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: 85.0%

: 1415098-72-4
(S)-1-benzyloxycarbonyl-6-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2,3,6-tetrahydropyridine

: 1415099-03-4
(2S,3R,4S)-1-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidine-3,4-diol

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; at 20 ℃; for 22h;
DOI:10.1039/c2ob26732b

Reference yield:

: 1415098-65-5
N-{(S)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]allyl}-3-buten-1-amine

: 1415099-03-4
(2S,3R,4S)-1-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidine-3,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

2: Grubbs catalyst first generation / dichloromethane / 2 h / 20 °C

3: water; 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone / 22 h / 20 °C

With Grubbs catalyst first generation; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetone; 3: |Upjohn Dihydroxylation;
DOI:10.1039/c2ob26732b

Reference yield:

: (S,E)-N-((2,2-dimethyl-1,3-dioxolan-4-yl)methylene)but-3-en-1-amine

: 1415099-03-4
(2S,3R,4S)-1-benzyloxycarbonyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]piperidine-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: boron trifluoride diethyl etherate / diethyl ether / 0.17 h / -20 °C / Inert atmosphere

1.2: -20 °C / Inert atmosphere

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C

3.1: Grubbs catalyst first generation / dichloromethane / 2 h / 20 °C

4.1: water; 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone / 22 h / 20 °C

With Grubbs catalyst first generation; osmium(VIII) oxide; boron trifluoride diethyl etherate; water; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; acetone; 4.1: |Upjohn Dihydroxylation;
DOI:10.1039/c2ob26732b