Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester
CAS No.:303082-33-9
Molecular Formula:C₄₄H₅₃NO₁₀Si
Molecular Weight:783.991
Hs Code.:

Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester

Synonyms:Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester

There total 4 articles about Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl 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: 83.0%

: 108-24-7
acetic anhydride

: 303082-32-8
Carbonic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-3-hydroxy-tetrahydro-pyran-4-yl ester 9H-fluoren-9-ylmethyl ester

: 303082-33-9
Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: With pyridine;
DOI:10.1021/ol006081l

Reference yield:

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 303082-33-9
Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / DMAP / pyridine / 20 °C

2: 91 percent / NaBH₃CN; HCl / diethyl ether; tetrahydrofuran

3: 83 percent / Py

With pyridine; hydrogenchloride; dmap; sodium cyanoborohydride; In tetrahydrofuran; pyridine; diethyl ether; 1: Acylation / 2: Ring cleavage / 3: Acetylation;
DOI:10.1021/ol006081l

Reference yield:

: 303082-31-7
dimethyl(thexyl)silyl 4,6-O-benzylidene-2-deoxy-2-(dimethylmaleimido)-β-D-glucopyranoside

: 303082-33-9
Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-5-(3,4-dimethyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-(9H-fluoren-9-ylmethoxycarbonyloxy)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / DMAP / pyridine / 20 °C

2: 91 percent / NaBH₃CN; HCl / diethyl ether; tetrahydrofuran

3: 83 percent / Py

With pyridine; hydrogenchloride; dmap; sodium cyanoborohydride; In tetrahydrofuran; pyridine; diethyl ether; 1: Acylation / 2: Ring cleavage / 3: Acetylation;
DOI:10.1021/ol006081l