(2S,3S)-3-Benzyloxy-3-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

Base Information

Chemical Name:(2S,3S)-3-Benzyloxy-3-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde
CAS No.:157219-97-1
Molecular Formula:C₂₂H₃₄O₅Si
Molecular Weight:406.594
Hs Code.:

Synonyms:(2S,3S)-3-Benzyloxy-3-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

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Chemical Property of (2S,3S)-3-Benzyloxy-3-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

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Technology Process of (2S,3S)-3-Benzyloxy-3-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

There total 16 articles about (2S,3S)-3-Benzyloxy-3-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde 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:

: 157219-96-0
(3R,4R,5S)-5-((1S,2S)-1-Benzyloxy-2-[1,3]dithian-2-yl-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one

: 157219-97-1
(2S,3S)-3-Benzyloxy-3-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

Guidance literature:: With N-iodo-succinimide; water; In acetonitrile; Ambient temperature;
DOI:10.1021/jo00083a008

Reference yield:

: 68907-47-1
methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

: 157219-97-1
(2S,3S)-3-Benzyloxy-3-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

Guidance literature:: Multi-step reaction with 12 steps

1.1: 99 percent / tetra-n-butylammonium iodide; sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 20 °C

2.1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

3.1: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

4.1: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

5.1: DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

5.2: 12.38 g / HCl / CH₂Cl₂; hexane; H₂O / 0.25 h

6.1: 14.79 g / 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 0.33 h / 20 °C

7.1: 8.03 g / triethylamine; phenylsulfonyl chloride / CH₂Cl₂ / 0 - 20 °C

8.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

9.1: 23.46 g / lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

10.1: 91 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / 0 °C

11.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 20 °C

12.1: N-iodosuccinimide / acetonitrile; H₂O / 0.17 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; benzenesulfonyl chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Alkylation / 2.1: Hydrolysis / 3.1: Tosylation / 4.1: Substitution / 5.1: Reduction / 5.2: Hydrolysis / 6.1: Oxidation / 7.1: Cyclization / 8.1: Metallation / 8.2: Methylation / 9.1: Metallation / 10.1: Ring cleavage / 11.1: Etherification / 12.1: Oxidation;
DOI:10.1021/jo990988j

Reference yield:

: 109958-35-2
(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 157219-97-1
(2S,3S)-3-Benzyloxy-3-[(2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-5-oxo-tetrahydro-furan-2-yl]-2-methyl-propionaldehyde

Guidance literature:: Multi-step reaction with 11 steps

1.1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

2.1: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

3.1: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

4.1: DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

4.2: 12.38 g / HCl / CH₂Cl₂; hexane; H₂O / 0.25 h

5.1: 14.79 g / 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 0.33 h / 20 °C

6.1: 8.03 g / triethylamine; phenylsulfonyl chloride / CH₂Cl₂ / 0 - 20 °C

7.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

8.1: 23.46 g / lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.1: 91 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / 0 °C

10.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 20 °C

11.1: N-iodosuccinimide / acetonitrile; H₂O / 0.17 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; benzenesulfonyl chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol; 1.1: Hydrolysis / 2.1: Tosylation / 3.1: Substitution / 4.1: Reduction / 4.2: Hydrolysis / 5.1: Oxidation / 6.1: Cyclization / 7.1: Metallation / 7.2: Methylation / 8.1: Metallation / 9.1: Ring cleavage / 10.1: Etherification / 11.1: Oxidation;
DOI:10.1021/jo990988j