(2R,3R,3aR,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one

Base Information

Chemical Name:(2R,3R,3aR,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one
CAS No.:158673-98-4
Molecular Formula:C₁₉H₂₆O₄Si
Molecular Weight:346.499
Hs Code.:

Synonyms:(2R,3R,3aR,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,3aR,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2R,3R,3aR,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one

There total 10 articles about (2R,3R,3aR,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-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:

: 156696-20-7
(2S,3S)-2-(4-methoxybenzyloxy)-3,4-O-(3-pentylidene)-1,3,4-butanetriol

: 158673-98-4
(2R,3R,3aR,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one

Guidance literature:: Multi-step reaction with 10 steps

1: 93 percent / pyridine / 9 h / 0 °C

2: 84 percent / CuI / tetrahydrofuran / 2 h / -30 °C

3: 96 percent / 2percent aq. H₂SO₄ / methanol / Ambient temperature

4: pyridine / 48 h / 0 °C

5: K₂CO₃ / methanol / 0.5 h / Ambient temperature

6: 87 percent / CuCN / diethyl ether / 2 h / -20 °C

7: 1.) O₃; 2.) Me₂S; 3.) PCC / 1.) acetone, from -78 deg C to -50 deg C, 90 min; 2.) acetone, r.t., overnight; 3.) CH₂Cl₂, 3 h, r.t.

8: 1.) BH₃*THF; 2.) 2M NaOH, H₂O₂ / 1.) THF, 0 deg C, 2 h; 2.) THF, H₂O, r.t., 1.5 h

9: 87 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

10: 1.) LDA, PhSeBr; 2.) pyridine, H₂O₂ / 1.) THF, -78 deg C, 40 min; 2.) ClCH₂CH₂Cl, refl., 3 h

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; copper(l) iodide; borane-THF; dimethylsulfide; sulfuric acid; Phenylselenyl bromide; dihydrogen peroxide; potassium carbonate; ozone; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)89432-1

Reference yield:

: (R)-2-((S)-1-((4-methoxybenzyl)oxy)pent-4-en-1-yl)oxirane

: 158673-98-4
(2R,3R,3aR,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / CuCN / diethyl ether / 2 h / -20 °C

2: 1.) O₃; 2.) Me₂S; 3.) PCC / 1.) acetone, from -78 deg C to -50 deg C, 90 min; 2.) acetone, r.t., overnight; 3.) CH₂Cl₂, 3 h, r.t.

3: 1.) BH₃*THF; 2.) 2M NaOH, H₂O₂ / 1.) THF, 0 deg C, 2 h; 2.) THF, H₂O, r.t., 1.5 h

4: 87 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

5: 1.) LDA, PhSeBr; 2.) pyridine, H₂O₂ / 1.) THF, -78 deg C, 40 min; 2.) ClCH₂CH₂Cl, refl., 3 h

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; borane-THF; dimethylsulfide; Phenylselenyl bromide; dihydrogen peroxide; ozone; pyridinium chlorochromate; lithium diisopropyl amide; In diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)89432-1

Reference yield:

: 158673-92-8
(2S,3S)-3-(4-Methoxy-benzyloxy)-hept-6-ene-1,2-diol

: 158673-98-4
(2R,3R,3aR,7aS)-3-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-2,3,3a,7a-tetrahydro-furo[3,2-b]pyran-5-one

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / 48 h / 0 °C

2: K₂CO₃ / methanol / 0.5 h / Ambient temperature

3: 87 percent / CuCN / diethyl ether / 2 h / -20 °C

4: 1.) O₃; 2.) Me₂S; 3.) PCC / 1.) acetone, from -78 deg C to -50 deg C, 90 min; 2.) acetone, r.t., overnight; 3.) CH₂Cl₂, 3 h, r.t.

5: 1.) BH₃*THF; 2.) 2M NaOH, H₂O₂ / 1.) THF, 0 deg C, 2 h; 2.) THF, H₂O, r.t., 1.5 h

6: 87 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / Ambient temperature

7: 1.) LDA, PhSeBr; 2.) pyridine, H₂O₂ / 1.) THF, -78 deg C, 40 min; 2.) ClCH₂CH₂Cl, refl., 3 h

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; borane-THF; dimethylsulfide; Phenylselenyl bromide; dihydrogen peroxide; potassium carbonate; ozone; pyridinium chlorochromate; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(01)89432-1