1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-lyxo-hex-4-ulose

Base Information

Chemical Name:1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-lyxo-hex-4-ulose
CAS No.:301649-57-0
Molecular Formula:C₂₇H₄₅NO₇Si
Molecular Weight:523.742
Hs Code.:

Synonyms:1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-lyxo-hex-4-ulose

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Chemical Property of 1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-lyxo-hex-4-ulose

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Technology Process of 1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-lyxo-hex-4-ulose

There total 7 articles about 1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-lyxo-hex-4-ulose 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: 93.0%

: 237388-06-6
1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol

: 301649-57-0
1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-lyxo-hex-4-ulose

Guidance literature:: With 1-methyl-pyrrolidin-2-one; molecular sieve; tetrapropylammonium perruthennate; In acetonitrile; at 20 ℃; for 2h;
DOI:10.1039/b001721n

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 301649-57-0
1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-lyxo-hex-4-ulose

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / imidazole / dimethylformamide / 24 h / 20 °C

2: 93 percent / NMP; TPAP; molecular sieves / acetonitrile / 2 h / 20 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; molecular sieve; tetrapropylammonium perruthennate; In N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Oxidation;
DOI:10.1039/b001721n

Reference yield:

: 22323-80-4
(4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 301649-57-0
1-O-Benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-lyxo-hex-4-ulose

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.33 h / -78 °C

1.2: 85 percent / hexane; tetrahydrofuran / 4 h / -78 - 20 °C

2.1: 77 percent / Na₂HPO₄; Na-Hg / methanol / 3 h / 0 °C

3.1: osmium tetraoxide; NMO; H₂O / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C

4.1: 95 percent / imidazole / dimethylformamide / 24 h / 20 °C

5.1: 93 percent / NMP; TPAP; molecular sieves / acetonitrile / 2 h / 20 °C

With 1H-imidazole; 1-methyl-pyrrolidin-2-one; disodium hydrogenphosphate; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; sodium amalgam; water; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Metallation / 1.2: Addition / 2.1: Elimination / 3.1: Oxidation / 4.1: Substitution / 5.1: Oxidation;
DOI:10.1039/b001721n