(2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-N,N-methoxymethylpropanamide

Base Information

Chemical Name:(2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-N,N-methoxymethylpropanamide
CAS No.:359849-32-4
Molecular Formula:C₃₁H₄₇NO₅Si
Molecular Weight:541.803
Hs Code.:

Synonyms:(2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-N,N-methoxymethylpropanamide

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Chemical Property of (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-N,N-methoxymethylpropanamide

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Technology Process of (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-N,N-methoxymethylpropanamide

There total 19 articles about (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-N,N-methoxymethylpropanamide 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: 63.0%

: 77-76-9
2,2-dimethoxy-propane

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

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

: 359849-32-4
(2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-N,N-methoxymethylpropanamide

Guidance literature:: With toluene-4-sulfonic acid; at 20 ℃; for 1h;
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

: 359849-32-4
(2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-N,N-methoxymethylpropanamide

Guidance literature:: Multi-step reaction with 17 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

17.1: 63 percent / p-TsOH / 1 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

: 359849-32-4
(2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-N,N-methoxymethylpropanamide

Guidance literature:: Multi-step reaction with 10 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

10.1: 63 percent / p-TsOH / 1 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium hydroxide; oxalyl dichloride; triethyl borane; iodine; trimethylaluminum; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; sodium hydrogencarbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; 2.1: Wittig reaction;
DOI:10.1021/jo010310f