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

Base Information

Chemical Name:(1S,2S,3R,6R)-6-(tert-butyldimethylsiloxy)-1-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-3-(p-methoxybenzyloxy)-4-cyclohexene-1,2-diol
CAS No.:778640-53-2
Molecular Formula:C₃₄H₅₅NO₈Si
Molecular Weight:633.898
Hs Code.:

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

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

Suppliers and Price of (1S,2S,3R,6R)-6-(tert-butyldimethylsiloxy)-1-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-3-(p-methoxybenzyloxy)-4-cyclohexene-1,2-diol

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

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

There total 12 articles about (1S,2S,3R,6R)-6-(tert-butyldimethylsiloxy)-1-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-3-(p-methoxybenzyloxy)-4-cyclohexene-1,2-diol 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

: 778640-53-2
(1S,2S,3R,6R)-6-(tert-butyldimethylsiloxy)-1-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-3-(p-methoxybenzyloxy)-4-cyclohexene-1,2-diol

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1002/anie.200454192 DOI:10.1055/s-2007-965893

Reference yield:

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

: 778640-53-2
(1S,2S,3R,6R)-6-(tert-butyldimethylsiloxy)-1-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-3-(p-methoxybenzyloxy)-4-cyclohexene-1,2-diol

Guidance literature:: Multi-step reaction with 7 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

7.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

With 2,6-dimethylpyridine; 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:

: 3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-D-arabinose

: 778640-53-2
(1S,2S,3R,6R)-6-(tert-butyldimethylsiloxy)-1-[(4S)-3-(tert-butoxycarbonyl-2,2-dimethyloxazolidin-4-yl)methyl]-1,2-O-isopropylidene-3-(p-methoxybenzyloxy)-4-cyclohexene-1,2-diol

Guidance literature:: Multi-step reaction with 11 steps

1.1: t-BuOK / benzene / 3 h / Heating

1.2: 86 percent / benzene; tetrahydrofuran / 1 h / Heating

2.1: 95 percent / oxalyl chloride; DMSO; i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 - 0 °C

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

4.1: 2.61 g / diethyl ether; methanol / 0.5 h / 20 °C

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

5.2: 69 percent / tetrahydrofuran / 4 h / -78 °C

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

6.2: tetrahydrofuran / 0.33 h / 0 °C

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

7.1: 475 mg / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

8.1: 88 percent / DIBAL-H / toluene; CH₂Cl₂ / 1 h / -100 °C

9.1: 93 percent / tetrahydrofuran / 1 h / 0 °C

10.1: 96 percent / [RuCl₂(=CHPh)(PCy₃)2] / CH₂Cl₂ / 12 h / Heating

11.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; benzene; 1.1: Wittig olefination / 1.2: Wittig olefination / 2.1: Swern oxidation / 9.1: Grignard reaction;
DOI:10.1055/s-2007-965893