1,5,6-Heptanetriol, 3-(4-hydroxy-3-methylphenyl)-6-methyl-, 1-acetate, (3S)-

Base Information

• Chemical Name: 1,5,6-Heptanetriol, 3-(4-hydroxy-3-methylphenyl)-6-methyl-, 1-acetate, (3S)-
• CAS No.: 850201-23-9
• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.39

Synonyms:

Chemical Property of 1,5,6-Heptanetriol, 3-(4-hydroxy-3-methylphenyl)-6-methyl-, 1-acetate, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5,6-Heptanetriol, 3-(4-hydroxy-3-methylphenyl)-6-methyl-, 1-acetate, (3S)-

There total 16 articles about 1,5,6-Heptanetriol, 3-(4-hydroxy-3-methylphenyl)-6-methyl-, 1-acetate, (3S)- 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:

3-(4-benzyloxy-3-methyl-phenyl)-pentanedioic acid dimethyl ester (532423-91-9) → Acetic acid (S)-5,6-dihydroxy-3-(4-hydroxy-3-methyl-phenyl)-6-methyl-heptyl ester (850201-23-9)

Guidance literature:

Multi-step reaction with 17 steps

1: PLE / dimethylsulfoxide

2: BOP; Et₃N

3: LiBH₄ / diethyl ether; ethanol

4: CSA / benzene

5: DIBAL-H / benzene

6: BF₃*OEt₂

7: 99 percent / imidazole / dimethylformamide

8: MeI; NaHCO₃ / acetonitrile; H₂O

9: NaBH₄ / ethanol

10: 86 percent / pyridine

11: 98 percent / TBAF / tetrahydrofuran

12: SO₃*pyr; DMSO; Et₃N / CH₂Cl₂

13: K₂CO₃; MeOH

14: 91 percent / nBuLi / tetrahydrofuran

15: 96 percent / pyridine

16: 100 percent / AD-mix-β

17: H₂ / Pd-C

With pyridine; 1H-imidazole; methanol; sodium tetrahydroborate; lithium borohydride; n-butyllithium; pyridine-SO₃ complex; AD-mix-β; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimethyl sulfoxide; triethylamine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene; 14: Wittig reaction / 16: Sharpless asymmetric dihydroxylation;

DOI:10.1016/S0040-4039(03)01094-3

Reference yield:

(R)-3-(4-Benzyloxy-3-methyl-phenyl)-5-hydroxy-pentanal → Acetic acid (S)-5,6-dihydroxy-3-(4-hydroxy-3-methyl-phenyl)-6-methyl-heptyl ester (850201-23-9)

Guidance literature:

Multi-step reaction with 12 steps

1: BF₃*OEt₂

2: 99 percent / imidazole / dimethylformamide

3: MeI; NaHCO₃ / acetonitrile; H₂O

4: NaBH₄ / ethanol

5: 86 percent / pyridine

6: 98 percent / TBAF / tetrahydrofuran

7: SO₃*pyr; DMSO; Et₃N / CH₂Cl₂

8: K₂CO₃; MeOH

9: 91 percent / nBuLi / tetrahydrofuran

10: 96 percent / pyridine

11: 100 percent / AD-mix-β

12: H₂ / Pd-C

With pyridine; 1H-imidazole; methanol; sodium tetrahydroborate; n-butyllithium; pyridine-SO₃ complex; AD-mix-β; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 9: Wittig reaction / 11: Sharpless asymmetric dihydroxylation;

DOI:10.1016/S0040-4039(03)01094-3

Reference yield:

(R)-4-(4-Benzyloxy-3-methyl-phenyl)-tetrahydro-pyran-2-one (603095-22-3) → Acetic acid (S)-5,6-dihydroxy-3-(4-hydroxy-3-methyl-phenyl)-6-methyl-heptyl ester (850201-23-9)

Guidance literature:

Multi-step reaction with 13 steps

1: DIBAL-H / benzene

2: BF₃*OEt₂

3: 99 percent / imidazole / dimethylformamide

4: MeI; NaHCO₃ / acetonitrile; H₂O

5: NaBH₄ / ethanol

6: 86 percent / pyridine

7: 98 percent / TBAF / tetrahydrofuran

8: SO₃*pyr; DMSO; Et₃N / CH₂Cl₂

9: K₂CO₃; MeOH

10: 91 percent / nBuLi / tetrahydrofuran

11: 96 percent / pyridine

12: 100 percent / AD-mix-β

13: H₂ / Pd-C

With pyridine; 1H-imidazole; methanol; sodium tetrahydroborate; n-butyllithium; pyridine-SO₃ complex; AD-mix-β; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; methyl iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 10: Wittig reaction / 12: Sharpless asymmetric dihydroxylation;

DOI:10.1016/S0040-4039(03)01094-3

upstream raw materials:

3-(4-benzyloxy-3-methyl-phenyl)-pentanedioic acid dimethyl ester

(R)-4-(4-Benzyloxy-3-methyl-phenyl)-tetrahydro-pyran-2-one

(R)-3-(4-Benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-en-1-ol

Acetic acid (S)-3-(4-benzyloxy-3-methyl-phenyl)-5-oxo-pentyl ester

Downstream raw materials:

Acetic acid (S)-3-(3-bromo-4-hydroxy-5-methyl-phenyl)-5,6-dihydroxy-6-methyl-heptyl ester

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