4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-(3(R,S)(5-phenylsulfinyl)-(E,E)-penta-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane

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Chemical Name:4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-(3(R,S)(5-phenylsulfinyl)-(E,E)-penta-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane
CAS No.:90623-38-4
Molecular Formula:C₂₁H₂₈O₅S
Molecular Weight:392.516
Hs Code.:

Synonyms:

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Chemical Property of 4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-(3(R,S)(5-phenylsulfinyl)-(E,E)-penta-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane

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Technology Process of 4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-(3(R,S)(5-phenylsulfinyl)-(E,E)-penta-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane

There total 15 articles about 4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-(3(R,S)(5-phenylsulfinyl)-(E,E)-penta-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane 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: 77.0%

: 90641-17-1,90694-56-7
8(R,S)-ethyl-7(R,S)-hydroxy-5(R,S)-(1(R,S)-hydroxy-6-(phenylsulfinyl)-(E,E)-hexa-2,4-dien-1-yl)-3,3,6(R,S),7-tetramethyl-1(R,S)-2,4,9-trioxabicyclo<4.3.0>nonane

: 90623-38-4,90693-98-4
4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-(3(R,S)(5-phenylsulfinyl)-(E,E)-penta-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; for 8h; Ambient temperature;
DOI:10.1021/ja00327a020

Reference yield:

: 20843-07-6
3,4-dimethylfuran

: 90623-38-4,90693-98-4
4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-(3(R,S)(5-phenylsulfinyl)-(E,E)-penta-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 12 steps

1: 63 percent / benzene; diethyl ether / 6 h / Irradiation

2: 80 percent / NaHCO₃ / CH₂Cl₂

3: 3 N HCl / tetrahydrofuran

4: MgSO₄ / CH₂Cl₂

5: tetrahydrofuran / 48 h / Ambient temperature

6: CuSO₄, CSA

7: 98 percent / Li, NH₃ / diethyl ether

8: 1) o-NO₂C₆H₄SeCN, Bu₃P, 2) H₂O₂ / 1) THF, 2) THF

9: O₃, NaHCO₃ / CH₂Cl₂; methanol / -78 °C

10: Me₂S / CH₂Cl₂; methanol / 3 h / Ambient temperature

11: 185 mg / 1.9 M n-BuLi/hexane / tetrahydrofuran / 0.67 h / -78 °C

12: 77 percent / camphorsulfonic acid / CH₂Cl₂ / 8 h / Ambient temperature

With hydrogenchloride; n-butyllithium; ortho-nitrophenyl selenocyanate; dimethylsulfide; hexane; tributylphosphine; camphor-10-sulfonic acid; ammonia; dihydrogen peroxide; lithium; sodium hydrogencarbonate; magnesium sulfate; ozone; copper(II) sulfate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;
DOI:10.1021/ja00327a020

Reference yield:

: 922-65-6
divinylcarbinol

: 90623-38-4,90693-98-4
4(R,S),6(R,S)-dihydroxy-5(R,S),6-dimethyl-7(R,S)-ethyl-(3(R,S)(5-phenylsulfinyl)-(E,E)-penta-1,3-dien-1-yl)-1(S,R)-2,8-dioxabicyclo<3.3.0>octane

Guidance literature:: Multi-step reaction with 3 steps

1: 1) n-BuLi / 1) THF, -78 deg C, 2) -50 --> 0 deg C

2: 185 mg / 1.9 M n-BuLi/hexane / tetrahydrofuran / 0.67 h / -78 °C

3: 77 percent / camphorsulfonic acid / CH₂Cl₂ / 8 h / Ambient temperature

With n-butyllithium; hexane; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00327a020