(3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-hexahydrobenzofuran-2(3H)-one

Base Information

Chemical Name:(3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-hexahydrobenzofuran-2(3H)-one
CAS No.:152492-18-7
Molecular Formula:C₂₃H₃₂O₅S₂
Molecular Weight:452.636
Hs Code.:

(3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-<bis(ethylthio)methyl>hexahydrobenzofuran-2(3H)-one

Synonyms:

Suppliers and Price of (3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-hexahydrobenzofuran-2(3H)-one

Supply Marketing:

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

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Total 2 raw suppliers

Chemical Property of (3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-hexahydrobenzofuran-2(3H)-one

Chemical Property:

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

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-hexahydrobenzofuran-2(3H)-one

There total 17 articles about (3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-hexahydrobenzofuran-2(3H)-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:

: 103537-73-1
(2R,3R,4R,5S)-4-(2-hydroxyethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

: 152492-18-7
(3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-hexahydrobenzofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 17 steps

1: 1.) Ph₃P, diethyl azodicarboxylate, 2.) MeI / 1.) THF, 0 deg C, 15 min, 2.) r.t., 8 h

2: NaH / tetrahydrofuran / 24 h / Heating

3: NaCl / dimethylsulfoxide; H₂O / 24 h / 160 °C

4: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

5: imidazole / dimethylformamide / 8 h / Ambient temperature

6: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 5 h, 2.) -78 deg C, 1 h

7: 1.) KN(TMS)2, 18-crown-6 / 1.) THF, toluene, -78 deg C, 20 min, 2.) THF, 5 deg C, 14 h

8: 100 percent / n-Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

9: 95 percent / PCC, molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

10: Sm(II) iodide, HMPA, 2-propanol / tetrahydrofuran / 1 h / Ambient temperature

11: 80 percent / 1M aq. HCl / tetrahydrofuran / 28 h / 5 °C

12: aq. NaIO₄ / methanol / 0.83 h / Ambient temperature

13: NaBH₄ / methanol / 0.67 h / 0 °C

14: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

15: 77 percent / 60percent aq. TFA / 72 h / 5 °C

16: aq. NaIO₄ / methanol / 4 h / Ambient temperature

17: conc. aq. HCl / 72 h / -15 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; molecular sieve; samarium diiodide; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; ozone; triphenylphosphine; isopropyl alcohol; pyridinium chlorochromate; trifluoroacetic acid; sodium chloride; diethylazodicarboxylate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00075a021

Reference yield:

: C₁₅H₂₀O₆

: 152492-18-7
(3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-hexahydrobenzofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄ / methanol / 0.67 h / 0 °C

2: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

3: 77 percent / 60percent aq. TFA / 72 h / 5 °C

4: aq. NaIO₄ / methanol / 4 h / Ambient temperature

5: conc. aq. HCl / 72 h / -15 °C

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; sodium hydride; trifluoroacetic acid; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00075a021

Reference yield:

: 146383-47-3
(2R,3R,4R,5S)-4-(2-Iodoethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran

: 152492-18-7
(3aS,4R,7aR)-4-<(1S)-2-(Benzyloxy)-1-(formyloxy)ethyl>-4-hexahydrobenzofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 16 steps

1: NaH / tetrahydrofuran / 24 h / Heating

2: NaCl / dimethylsulfoxide; H₂O / 24 h / 160 °C

3: 100 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

4: imidazole / dimethylformamide / 8 h / Ambient temperature

5: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 5 h, 2.) -78 deg C, 1 h

6: 1.) KN(TMS)2, 18-crown-6 / 1.) THF, toluene, -78 deg C, 20 min, 2.) THF, 5 deg C, 14 h

7: 100 percent / n-Bu₄NF / tetrahydrofuran / 4 h / Ambient temperature

8: 95 percent / PCC, molecular sieves / CH₂Cl₂ / 0.5 h / Ambient temperature

9: Sm(II) iodide, HMPA, 2-propanol / tetrahydrofuran / 1 h / Ambient temperature

10: 80 percent / 1M aq. HCl / tetrahydrofuran / 28 h / 5 °C

11: aq. NaIO₄ / methanol / 0.83 h / Ambient temperature

12: NaBH₄ / methanol / 0.67 h / 0 °C

13: 89 percent / NaH / dimethylformamide / 2 h / Ambient temperature

14: 77 percent / 60percent aq. TFA / 72 h / 5 °C

15: aq. NaIO₄ / methanol / 4 h / Ambient temperature

16: conc. aq. HCl / 72 h / -15 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; molecular sieve; samarium diiodide; 18-crown-6 ether; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; ozone; triphenylphosphine; isopropyl alcohol; pyridinium chlorochromate; trifluoroacetic acid; sodium chloride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00075a021