tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate

Base Information

Chemical Name:tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate
CAS No.:359849-25-5
Molecular Formula:C₃₁H₄₃IO₆Si
Molecular Weight:666.669
Hs Code.:

Synonyms:tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate

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Chemical Property of tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate

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Technology Process of tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate

There total 14 articles about tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate 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:

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

: 359849-25-5
tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate

Guidance literature:: Multi-step reaction with 13 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

With 1H-imidazole; hydrogenchloride; lithium hydroxide; oxalyl dichloride; triethyl borane; iodine; 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:

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

: 359849-25-5
tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate

Guidance literature:: Multi-step reaction with 5 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

With 1H-imidazole; hydrogenchloride; iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 1.1: 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

: 359849-25-5
tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; hydrogenchloride; oxalyl dichloride; iodine; silver trifluoromethanesulfonate; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 2.1: Wittig reaction;
DOI:10.1021/jo010310f