(1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol

Base Information

Chemical Name:(1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol
CAS No.:778640-44-1
Molecular Formula:C₂₈H₄₁NO₈
Molecular Weight:519.635
Hs Code.:

(1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol

Synonyms:(1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol

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Chemical Property of (1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol

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Technology Process of (1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol

There total 11 articles about (1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol 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: 96.0%

: 778640-37-2
(3R,4R,5S,6R)-4-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-4,5-O-isopropylidene-6-(p-methoxybenzyloxy)-1,7-octadiene-3,4,5-triol

: 778640-44-1
(1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; for 12h; Heating;
DOI:10.1002/anie.200454192

Reference yield:

: 95715-87-0
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

: 778640-44-1
(1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

1.2: 69 percent / tetrahydrofuran / 4 h / -78 °C

2.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

2.2: tetrahydrofuran / 0.33 h / 0 °C

2.3: tetrahydrofuran / 0.5 h / 0 - 20 °C

3.1: 475 mg / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

4.1: 88 percent / DIBAL-H / toluene; CH₂Cl₂ / 1 h / -100 °C

5.1: 93 percent / tetrahydrofuran / 1 h / 0 °C

6.1: 96 percent / [RuCl₂(=CHPh)(PCy₃)2] / CH₂Cl₂ / 12 h / Heating

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; toluene; 5.1: Grignard reaction;
DOI:10.1055/s-2007-965893

Reference yield:

: 778640-51-0
(2S,3S,4R)-2,3-O-isopropylidenedioxy-4-(p-methoxybenzyloxy)-5-hexenal

: 778640-44-1
(1S,2R,3R,6R)-2-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-6-(p-methoxybenzyloxy)-4-cyclohexene-1,2,3-triol

Guidance literature:: Multi-step reaction with 8 steps

1.1: NaClO₂; NaH₂PO₄ / dimethylsulfoxide; H₂O / 1 h / 20 °C

2.1: 2.61 g / diethyl ether; methanol / 0.5 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

3.2: 69 percent / tetrahydrofuran / 4 h / -78 °C

4.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

4.2: tetrahydrofuran / 0.33 h / 0 °C

4.3: tetrahydrofuran / 0.5 h / 0 - 20 °C

5.1: 475 mg / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

6.1: 88 percent / DIBAL-H / toluene; CH₂Cl₂ / 1 h / -100 °C

7.1: 93 percent / tetrahydrofuran / 1 h / 0 °C

8.1: 96 percent / [RuCl₂(=CHPh)(PCy₃)2] / CH₂Cl₂ / 12 h / Heating

With sodium chlorite; sodium dihydrogenphosphate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; 7.1: Grignard reaction;
DOI:10.1055/s-2007-965893