ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate

Base Information

Chemical Name:ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate
CAS No.:221564-65-4
Molecular Formula:C₁₉H₂₉NO₈S
Molecular Weight:431.507
Hs Code.:

Synonyms:ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate

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Chemical Property of ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate

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Technology Process of ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate

There total 5 articles about ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate 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: 82.0%

: 221564-64-3
(3S,6R,1'S,2'S,3'S)-3-(1-benzyloxy-2,3-isopropylidenedioxy-4-(methanesulfonyl)oxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

: 221564-65-4
ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate

Guidance literature:: With hydrogenchloride; In ethanol; at 20 ℃; for 9h;
DOI:10.1021/jo702601z

Reference yield:

: 101331-92-4
4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-L-threose

: 221564-65-4
ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 79 percent / SnCl₂ / tetrahydrofuran / 1 h / -78 °C

2: 75 percent / NaH, Bu₄NI / 24 h / Ambient temperature

3: 95 percent / Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

4: Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

5: 65 percent / 0.25 M HCl / ethanol / 9 h

With hydrogenchloride; dmap; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; tin(ll) chloride; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/S0040-4039(99)00107-0

Reference yield:

: 221564-63-2
(3S,6R,1'S,2'S,3'S)-3-(1-benzyloxy-4-hydroxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine

: 221564-65-4
ethyl (2S,3S,4S,5S)-2-amino-3-benzyloxy-4,5-isopropylidenedioxy-6-(methanesulfonyl)oxyhexanoate

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N, DMAP / CH₂Cl₂ / 1 h / Ambient temperature

2: 65 percent / 0.25 M HCl / ethanol / 9 h

With hydrogenchloride; dmap; triethylamine; In ethanol; dichloromethane;
DOI:10.1016/S0040-4039(99)00107-0