methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

Base Information

Chemical Name:methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate
CAS No.:916154-72-8
Molecular Formula:C₃₈H₄₂N₆O₉
Molecular Weight:726.786
Hs Code.:

Synonyms:methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

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Chemical Property of methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

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Technology Process of methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

There total 6 articles about methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate 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: 77.0%

: 916154-77-3
6-N,N-dibenzoyl-5'-deoxy-5'-methylene-2,3-O-isopropylideneadenosine

: 92136-57-7
(S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester

: 916154-72-8
methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 65 ℃;
DOI:10.1021/ol062026m

Reference yield:

: 65969-38-2
5'-deoxy-2',3'-O-isopropylidene-5'-methyleneadenosine

: 916154-72-8
methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / pyridine / 0 - 20 °C

2: 77 percent / 1,3-(bis-mesityl-2-imidazolidinylidene)(o-iPrO-PhCH=)RuCl₂ / CH₂Cl₂ / 65 °C

With pyridine; Hoveyda-Grubbs catalyst second generation; In dichloromethane;
DOI:10.1021/ol062026m

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 916154-72-8
methyl 2(S)-tert-butoxycarbonylamino-5(E)-[6-N,N-dibenzoyl-5'-deoxy-2',3'-O-isopropylideneadenosin-5'-ylidene]pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 79 percent / NaHCO₃ / dioxane; H₂O / 18 h / 20 °C

2: 49 percent / α-chymotrypsin / aq. phosphate buffer / 24 h / 37 °C / pH 8.00

3: 93 percent / ethanol / 0.5 h / 20 °C

4: 77 percent / 1,3-(bis-mesityl-2-imidazolidinylidene)(o-iPrO-PhCH=)RuCl₂ / CH₂Cl₂ / 65 °C

With Hoveyda-Grubbs catalyst second generation; sodium hydrogencarbonate; α-chymotrypsin; In 1,4-dioxane; phosphate buffer; ethanol; dichloromethane; water;
DOI:10.1021/ol062026m