(2R,3R,4R,5R,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-dihydroxy-N,N-methoxymethyl-2,4,6-trimethylheptamide

Base Information

Chemical Name:(2R,3R,4R,5R,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-dihydroxy-N,N-methoxymethyl-2,4,6-trimethylheptamide
CAS No.:359849-30-2
Molecular Formula:C₂₈H₄₃NO₅Si
Molecular Weight:501.739
Hs Code.:

Synonyms:(2R,3R,4R,5R,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-dihydroxy-N,N-methoxymethyl-2,4,6-trimethylheptamide

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Chemical Property of (2R,3R,4R,5R,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-dihydroxy-N,N-methoxymethyl-2,4,6-trimethylheptamide

Chemical Property:

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Technology Process of (2R,3R,4R,5R,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-dihydroxy-N,N-methoxymethyl-2,4,6-trimethylheptamide

There total 18 articles about (2R,3R,4R,5R,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-dihydroxy-N,N-methoxymethyl-2,4,6-trimethylheptamide 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: 95.0%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 359849-29-9
(3R,4R,5S,6R)-6-[(1R)-2-(tert-butyldiphenylsilyloxy-1-methylethyl)]-4-hydroxy-3,5-dimethyltetrahydropyran-2-one

: 359849-30-2
(2R,3R,4R,5R,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-dihydroxy-N,N-methoxymethyl-2,4,6-trimethylheptamide

Guidance literature:: N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In hexane; dichloromethane; at 20 ℃; for 1h;

(3R,4R,5S,6R)-6-[(1R)-2-(tert-butyldiphenylsilyloxy-1-methylethyl)]-4-hydroxy-3,5-dimethyltetrahydropyran-2-one; In dichloromethane; at 20 ℃; for 0.5h; Further stages.;
DOI:10.1021/jo010310f

Reference yield:

: 359849-10-8
tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate

: 359849-30-2
(2R,3R,4R,5R,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-dihydroxy-N,N-methoxymethyl-2,4,6-trimethylheptamide

Guidance literature:: Multi-step reaction with 16 steps

1.1: MgBr₂*OEt₂; Bu₃SnH; Et₃B / tetrahydrofuran; hexane / 0 °C

2.1: CH₂Cl₂ / 1 h / 20 °C

2.2: 98 percent / aq. K₂CO₃ / 2-methyl-propan-2-ol / 6 h / Heating

3.1: 70 percent / NaHCO₃; AgOTf; I₂ / acetonitrile / 20 °C

4.1: 99 percent / Bu₃SnH; Et₃B / tetrahydrofuran; hexane / 0.67 h / -78 °C

5.1: 95 percent / LiOH / tetrahydrofuran; H₂O / 2 h / 0 °C

6.1: 85 percent / p-TsOH / 2 h / 20 °C

7.1: 63 percent / DIBAL / tetrahydrofuran; hexane / 24 h / -78 - 20 °C

8.1: 99 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

9.1: 60 percent / toluene / 6 h / Heating

10.1: 92 percent / HCl / tetrahydrofuran / 2 h / 20 °C

11.1: 89 percent / imidazole / CH₂Cl₂ / 2 h / 0 °C

12.1: CH₂Cl₂ / 0.5 h / 20 °C

12.2: 86 percent / aq. K₂CO₃ / 2-methyl-propan-2-ol / 6 h / Heating

13.1: 60 percent / NaHCO₃; AgOTf; I₂ / acetonitrile / 3 h / 20 °C

14.1: 89 percent / Bu₃SnH; Et₃B / tetrahydrofuran; hexane / 3 h / -78 °C

15.1: 77 percent / LiOH / tetrahydrofuran; H₂O / 5 h / 0 °C

16.1: Me₃Al / CH₂Cl₂; hexane / 1 h / 20 °C

16.2: 95 percent / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium hydroxide; oxalyl dichloride; triethyl borane; iodine; trimethylaluminum; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; magnesium bromide; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; 9.1: Wittig reaction;
DOI:10.1021/jo010310f

Reference yield:

: 76156-31-5
(S)-2-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxan-4-yl)-propan-1-ol

: 359849-30-2
(2R,3R,4R,5R,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-dihydroxy-N,N-methoxymethyl-2,4,6-trimethylheptamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 60 percent / toluene / 6 h / Heating

3.1: 92 percent / HCl / tetrahydrofuran / 2 h / 20 °C

4.1: 89 percent / imidazole / CH₂Cl₂ / 2 h / 0 °C

5.1: CH₂Cl₂ / 0.5 h / 20 °C

5.2: 86 percent / aq. K₂CO₃ / 2-methyl-propan-2-ol / 6 h / Heating

6.1: 60 percent / NaHCO₃; AgOTf; I₂ / acetonitrile / 3 h / 20 °C

7.1: 89 percent / Bu₃SnH; Et₃B / tetrahydrofuran; hexane / 3 h / -78 °C

8.1: 77 percent / LiOH / tetrahydrofuran; H₂O / 5 h / 0 °C

9.1: Me₃Al / CH₂Cl₂; hexane / 1 h / 20 °C

9.2: 95 percent / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium hydroxide; oxalyl dichloride; triethyl borane; iodine; trimethylaluminum; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; 2.1: Wittig reaction;
DOI:10.1021/jo010310f