(S)-2-(tert-butoxycarbonylamino)-3-(4-(β-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

Base Information

Chemical Name:(S)-2-(tert-butoxycarbonylamino)-3-(4-(β-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester
CAS No.:1435781-18-2
Molecular Formula:C₃₃H₄₅NO₁₄S
Molecular Weight:711.785
Hs Code.:

Synonyms:(S)-2-(tert-butoxycarbonylamino)-3-(4-(β-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

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Chemical Property of (S)-2-(tert-butoxycarbonylamino)-3-(4-(β-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

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Technology Process of (S)-2-(tert-butoxycarbonylamino)-3-(4-(β-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

There total 3 articles about (S)-2-(tert-butoxycarbonylamino)-3-(4-(β-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester 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:

: 150438-79-2
benzyl O-allyl-N-(tert-butoxycarbonyl)-L-serinate

: allyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-D-glucopyranoside

: 1435781-18-2
(S)-2-(tert-butoxycarbonylamino)-3-(4-(β-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

: 1435781-14-8
(S)-2-(tert-butoxycarbonylamino)-3-(4-(α-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; In toluene; at 80 ℃; for 33h; Overall yield = 47%; Overall yield = 50.0 mg;
DOI:10.1016/j.carres.2013.02.013

Reference yield:

: 100-51-6,185532-71-2
benzyl alcohol

: 1435781-18-2
(S)-2-(tert-butoxycarbonylamino)-3-(4-(β-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

: 1435781-14-8
(S)-2-(tert-butoxycarbonylamino)-3-(4-(α-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: dmap / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

1.2: 24 h / 0 - 20 °C / Inert atmosphere

2.1: Hoveyda-Grubbs catalyst second generation / toluene / 33 h / 80 °C

With dmap; Hoveyda-Grubbs catalyst second generation; In dichloromethane; toluene;
DOI:10.1016/j.carres.2013.02.013

Reference yield:

: 150438-78-1
(2S)-3-allyloxy-2-tert-butoxycarbonylaminopropionic acid

: 1435781-18-2
(S)-2-(tert-butoxycarbonylamino)-3-(4-(β-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

: 1435781-14-8
(S)-2-(tert-butoxycarbonylamino)-3-(4-(α-D-tetra-O-acetylglucosylthio)-(E)-but-2-enyloxy)propanoate benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: dmap / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

1.2: 24 h / 0 - 20 °C / Inert atmosphere

2.1: Hoveyda-Grubbs catalyst second generation / toluene / 33 h / 80 °C

With dmap; Hoveyda-Grubbs catalyst second generation; In dichloromethane; toluene;
DOI:10.1016/j.carres.2013.02.013