(3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[octahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxo-3'-(phenylthio)spiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate

Base Information

• Chemical Name: (3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[octahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxo-3'-(phenylthio)spiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate
• CAS No.: 117897-41-3
• Molecular Formula: C₂₇H₃₇NO₆S
• Molecular Weight: 503.66
• Mol file: 117897-41-3.mol

Synonyms:

Chemical Property of (3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[octahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxo-3'-(phenylthio)spiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[octahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxo-3'-(phenylthio)spiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate

There total 12 articles about (3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[octahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxo-3'-(phenylthio)spiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate 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: 89.0%

thiophenol (108-98-5) + (3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[3'-ethoxyoctahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxospiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate (117897-40-2,117957-22-9) → (3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[octahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxo-3'-(phenylthio)spiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate (117897-41-3,117957-23-0)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1021/ja970089h

Reference yield:

2-[(5-oxo-3(E)-hexenyl)oxy]tetrahydropyran (117897-32-2) → (3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[octahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxo-3'-(phenylthio)spiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate (117897-41-3,117957-23-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / LDA / tetrahydrofuran / -78 deg C, 50 min, rt, 4 h

2: toluene / 16 h / Heating

3: p-toluenesulfonic acid monohydrate / toluene / 16 h / Heating

4: 1.) o-NO₂C₆H₄SeCN, n-Bu₃P, 2.) Na₂HPO₄, aq. H₂O₂ / 1.) THF, 0 deg C to rt, 2.25 h, 2.) 40 deg C, 1 h, rt, 12 h

5: 80 percent / NaBH₄ / methanol / -23 deg C, 30 min, rt, 2 h

6: 79 percent / NaH / tetrahydrofuran / 5 h / 30 - 45 °C

7: 88 percent / LDA / tetrahydrofuran

8: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH

10: 89 percent / p-TsOH / CH₂Cl₂

With sodium tetrahydroborate; disodium hydrogenphosphate; ortho-nitrophenyl selenocyanate; dimethylsulfide; tributylphosphine; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; ozone; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ja970089h

Reference yield:

2-({5-[(trimethylsilyl)oxy]-3(E),5-hexadienyl}oxy)tetrahydropyran (117897-33-3) → (3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[octahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxo-3'-(phenylthio)spiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate (117897-41-3,117957-23-0)

Guidance literature:

Multi-step reaction with 9 steps

1: toluene / 16 h / Heating

2: p-toluenesulfonic acid monohydrate / toluene / 16 h / Heating

3: 1.) o-NO₂C₆H₄SeCN, n-Bu₃P, 2.) Na₂HPO₄, aq. H₂O₂ / 1.) THF, 0 deg C to rt, 2.25 h, 2.) 40 deg C, 1 h, rt, 12 h

4: 80 percent / NaBH₄ / methanol / -23 deg C, 30 min, rt, 2 h

5: 79 percent / NaH / tetrahydrofuran / 5 h / 30 - 45 °C

6: 88 percent / LDA / tetrahydrofuran

7: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH

9: 89 percent / p-TsOH / CH₂Cl₂

With sodium tetrahydroborate; disodium hydrogenphosphate; ortho-nitrophenyl selenocyanate; dimethylsulfide; tributylphosphine; dihydrogen peroxide; sodium hydride; toluene-4-sulfonic acid; ozone; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ja970089h

upstream raw materials:

thiophenol

C₂₃H₃₇NO₇

(3'α,3'aα,7'β(E),7'aα)-(+/-)-ethyl 3-[3'-ethoxyoctahydro-7'a-(methoxymethyl)-2',5,5-trimethyl-1'-oxospiro[1,3-dioxane-2,5'-[5H]isoindol]-7'-yl]-2-propenoate

2-[(5-oxo-3(E)-hexenyl)oxy]tetrahydropyran

Downstream raw materials:

(1α,3aα,4β(E),7'aα)-(+/-)-ethyl 3-isoindol-4-yl>-2-propenoate