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

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]-5-[1,3]dioxolanepentan-3-one
• CAS No.: 359849-33-5
• Molecular Formula: C₃₄H₅₀O₆Si
• Molecular Weight: 582.853

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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]-5-[1,3]dioxolanepentan-3-one 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:

tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate (359849-10-8) → (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-one (359849-33-5)

Guidance literature:

Multi-step reaction with 18 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

18.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C

18.2: 65 percent / diethyl ether / 0.33 h / 20 °C

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

DOI:10.1021/jo010310f

Reference yield:

(2R)-2-[(4R,5R)-2,2,5-trimethyl[1,3]dioxan-4-yl]propionaldehyde (76123-21-2,79055-70-2,83434-14-4,83434-15-5,83434-16-6,83434-17-7,96554-52-8,97058-14-5,97805-14-6,110715-70-3,133006-96-9,81470-93-1) → (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-one (359849-33-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 60 percent / toluene / 6 h / Heating

2.1: 92 percent / HCl / tetrahydrofuran / 2 h / 20 °C

3.1: 89 percent / imidazole / CH₂Cl₂ / 2 h / 0 °C

4.1: CH₂Cl₂ / 0.5 h / 20 °C

4.2: 86 percent / aq. K₂CO₃ / 2-methyl-propan-2-ol / 6 h / Heating

5.1: 60 percent / NaHCO₃; AgOTf; I₂ / acetonitrile / 3 h / 20 °C

6.1: 89 percent / Bu₃SnH; Et₃B / tetrahydrofuran; hexane / 3 h / -78 °C

7.1: 77 percent / LiOH / tetrahydrofuran; H₂O / 5 h / 0 °C

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

8.2: 95 percent / CH₂Cl₂ / 0.5 h / 20 °C

9.1: 63 percent / p-TsOH / 1 h / 20 °C

10.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C

10.2: 65 percent / diethyl ether / 0.33 h / 20 °C

With 1H-imidazole; hydrogenchloride; lithium hydroxide; triethyl borane; iodine; trimethylaluminum; tert.-butyl lithium; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; pentane; 1.1: Wittig reaction;

DOI:10.1021/jo010310f

Reference yield:

(S)-2-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxan-4-yl)-propan-1-ol (76156-31-5) → (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-one (359849-33-5)

Guidance literature:

Multi-step reaction with 11 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

11.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C

11.2: 65 percent / diethyl ether / 0.33 h / 20 °C

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

DOI:10.1021/jo010310f

upstream raw materials:

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

(2R)-2-[(4R,5R)-2,2,5-trimethyl[1,3]dioxan-4-yl]propionaldehyde

tert-butylchlorodiphenylsilane

tert-butyl (4S)-5-hydroxy-2,4-dimethylpent-2-enoate

Downstream raw materials:

(2S,3R)-3-benzyloxymethoxy-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentane

(2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol

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