2,2-Dimethyl-propionic acid (1S,4S,5R)-6-[1,3]dithian-2-yl-1-isopropenyl-5-(4-methoxy-benzyloxy)-4-methyl-hexyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (1S,4S,5R)-6-[1,3]dithian-2-yl-1-isopropenyl-5-(4-methoxy-benzyloxy)-4-methyl-hexyl ester
• CAS No.: 187528-69-4
• Molecular Formula: C₂₇H₄₂O₄S₂
• Molecular Weight: 494.76

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (1S,4S,5R)-6-[1,3]dithian-2-yl-1-isopropenyl-5-(4-methoxy-benzyloxy)-4-methyl-hexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (1S,4S,5R)-6-[1,3]dithian-2-yl-1-isopropenyl-5-(4-methoxy-benzyloxy)-4-methyl-hexyl ester

There total 14 articles about 2,2-Dimethyl-propionic acid (1S,4S,5R)-6-[1,3]dithian-2-yl-1-isopropenyl-5-(4-methoxy-benzyloxy)-4-methyl-hexyl ester 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:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → 2,2-Dimethyl-propionic acid (1S,4S,5R)-6-[1,3]dithian-2-yl-1-isopropenyl-5-(4-methoxy-benzyloxy)-4-methyl-hexyl ester (187528-69-4)

Guidance literature:

Multi-step reaction with 9 steps

1: CF₃SO₃H / tetrahydrofuran

2: 2 M NaOH / ethanol

3: CBr₄, PPh₃ / CH₂Cl₂

4: n-BuLi / tetrahydrofuran / -30 °C

5: PPTS, MeOH

6: DMAP / pyridine

7: K₂CO₃ / methanol

8: (i-PrO)3Al / toluene / 120 °C

9: Et₃N, DMAP / CH₂Cl₂

With methanol; dmap; sodium hydroxide; n-butyllithium; carbon tetrabromide; trifluorormethanesulfonic acid; pyridinium p-toluenesulfonate; aluminum isopropoxide; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; toluene;

DOI:10.1246/cl.1997.117

Reference yield:

(3S,6R)-6,7-dihydroxy-3,7-dimethyloctyl acetate (130647-99-3) → 2,2-Dimethyl-propionic acid (1S,4S,5R)-6-[1,3]dithian-2-yl-1-isopropenyl-5-(4-methoxy-benzyloxy)-4-methyl-hexyl ester (187528-69-4)

Guidance literature:

Multi-step reaction with 14 steps

1: PPTS / CH₂Cl₂

2: K₂CO₃, MeOH

3: NaH, Bu₄NI / tetrahydrofuran

4: 83 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C

5: 1) AD-mix-α, 2) DMAP, DCC / 1) H2O, t-BuOH, 0 deg C, 2) CH2Cl2

6: CF₃SO₃H / tetrahydrofuran

7: 2 M NaOH / ethanol

8: CBr₄, PPh₃ / CH₂Cl₂

9: n-BuLi / tetrahydrofuran / -30 °C

10: PPTS, MeOH

11: DMAP / pyridine

12: K₂CO₃ / methanol

13: (i-PrO)3Al / toluene / 120 °C

14: Et₃N, DMAP / CH₂Cl₂

With methanol; dmap; sodium hydroxide; AD-mix-α; n-butyllithium; carbon tetrabromide; trifluorormethanesulfonic acid; pyridinium p-toluenesulfonate; aluminum isopropoxide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; toluene;

DOI:10.1246/cl.1997.117

Reference yield:

(S)-3-Methyl-5-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-pentan-1-ol (114905-28-1) → 2,2-Dimethyl-propionic acid (1S,4S,5R)-6-[1,3]dithian-2-yl-1-isopropenyl-5-(4-methoxy-benzyloxy)-4-methyl-hexyl ester (187528-69-4)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH, Bu₄NI / tetrahydrofuran

2: 83 percent / n-BuLi / tetrahydrofuran / -78 - 0 °C

3: 1) AD-mix-α, 2) DMAP, DCC / 1) H2O, t-BuOH, 0 deg C, 2) CH2Cl2

4: CF₃SO₃H / tetrahydrofuran

5: 2 M NaOH / ethanol

6: CBr₄, PPh₃ / CH₂Cl₂

7: n-BuLi / tetrahydrofuran / -30 °C

8: PPTS, MeOH

9: DMAP / pyridine

10: K₂CO₃ / methanol

11: (i-PrO)3Al / toluene / 120 °C

12: Et₃N, DMAP / CH₂Cl₂

With methanol; dmap; sodium hydroxide; AD-mix-α; n-butyllithium; carbon tetrabromide; trifluorormethanesulfonic acid; pyridinium p-toluenesulfonate; aluminum isopropoxide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; toluene;

DOI:10.1246/cl.1997.117

upstream raw materials:

(3S,6R)-6,7-dihydroxy-3,7-dimethyloctyl acetate

O-(4-methoxybenzyl)-trichloroacetimidate

(S)-3-Methyl-5-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-pentan-1-ol

(R)-2,2,4,4-Tetramethyl-5-((S)-3-methyl-pent-4-enyl)-[1,3]dioxolane

Downstream raw materials:

Acetic acid (1S,4S,5R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-7-hydroxy-5-(4-methoxy-benzyloxy)-4-methyl-heptyl ester

(2R,3S,6S,7R)-1-(tert-Butyl-diphenyl-silanyloxy)-8-[1,3]dithian-2-yl-7-(4-methoxy-benzyloxy)-2,6-dimethyl-octan-3-ol

(2R,3S,6S,7R)-8-[1,3]Dithian-2-yl-7-(4-methoxy-benzyloxy)-2,6-dimethyl-octane-1,3-diol

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