4-O-Acetyl-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol

Base Information

Chemical Name:4-O-Acetyl-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol
CAS No.:237388-07-7
Molecular Formula:C₂₉H₄₉NO₈Si
Molecular Weight:567.795
Hs Code.:

Synonyms:4-O-Acetyl-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol

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Chemical Property of 4-O-Acetyl-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol

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Technology Process of 4-O-Acetyl-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol

There total 10 articles about 4-O-Acetyl-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol 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: 80.0%

: 108-24-7
acetic anhydride

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

: 237388-07-7
4-O-Acetyl-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol

Guidance literature:: With dmap; triethylamine; at 50 ℃; for 8h;
DOI:10.1016/S0040-4039(99)00978-8

Reference yield:

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

: 237388-07-7
4-O-Acetyl-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol

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: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

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

Reference yield:

: 237388-03-3
(2S,5S)-6-Benzyloxy-5-[(tert-butoxycarbonyl)amino]-1,2-isopropylidenedioxy-4-(phenylsulfonyl)hexan-3-ol

: 237388-07-7
4-O-Acetyl-1-O-benzyl-2-[(tert-butoxycarbonyl)amino]-3-O-(tert-butyldimethylsilyl)-2-deoxy-5,6-isopropylidene-L-mannitol

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / Na₂HPO₄; Na-Hg / methanol / 3 h / 0 °C

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

3: 95 percent / imidazole / dimethylformamide / 24 h / 20 °C

4: 80 percent / Et₃N; DMAP / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; dmap; disodium hydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium amalgam; water; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Elimination / 2: Oxidation / 3: Substitution / 4: Acetylation;
DOI:10.1039/b001721n