[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester

Base Information

• Chemical Name: [(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester
• CAS No.: 790699-97-7
• Molecular Formula: C₂₃H₃₆O₅
• Molecular Weight: 392.536

Synonyms:[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester

Chemical Property of [(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester

There total 17 articles about [(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl 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:

benzyl bromide (100-39-0) → [(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester (790699-97-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 92 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 1.5 h / 0 °C

2.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: 62 percent / LiCl; NaBH₄ / ethanol; tetrahydrofuran / 72 h / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

7.1: n-BuLi / tetrahydrofuran; CH₂Cl₂ / 0.5 h / -78 - 0 °C

7.2: tetrahydrofuran / 1 h / -78 - 0 °C

8.1: 62 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

9.1: Ti(OiPr)4; (+)-DIPT; 4A MS / TBHP / CH₂Cl₂ / 0.67 h / -23 °C

10.1: mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

11.1: 60 percent / Zn; ZnCl₂ / cp2TiCl₂ / tetrahydrofuran / 6 h / -20 - 20 °C

12.1: 94 percent / CSA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

13.1: 93 percent / TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

14.1: SO₃*py; Et₃N / dimethylsulfoxide / 1 h / 0 - 20 °C

14.2: NaClO₂; Na₂HPO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1.5 h / 20 °C

15.1: diethyl ether / 0.25 h / 0 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; zinc(II) chloride; zinc; tert.-butylhydroperoxide; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 3.1: Swern oxidation / 6.1: Swern oxidation / 7.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2004.08.099

Reference yield:

(S)-pentane-1,3-diol (790699-26-2) → [(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester (790699-97-7)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: 92 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 1.5 h / 0 °C

3.1: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h / 0 - 20 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

5.1: CH₂Cl₂ / 3 h / 0 - 20 °C

6.1: 62 percent / LiCl; NaBH₄ / ethanol; tetrahydrofuran / 72 h / 20 °C

7.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

8.1: n-BuLi / tetrahydrofuran; CH₂Cl₂ / 0.5 h / -78 - 0 °C

8.2: tetrahydrofuran / 1 h / -78 - 0 °C

9.1: 62 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

10.1: Ti(OiPr)4; (+)-DIPT; 4A MS / TBHP / CH₂Cl₂ / 0.67 h / -23 °C

11.1: mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

12.1: 60 percent / Zn; ZnCl₂ / cp2TiCl₂ / tetrahydrofuran / 6 h / -20 - 20 °C

13.1: 94 percent / CSA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

14.1: 93 percent / TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

15.1: SO₃*py; Et₃N / dimethylsulfoxide / 1 h / 0 - 20 °C

15.2: NaClO₂; Na₂HPO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1.5 h / 20 °C

16.1: diethyl ether / 0.25 h / 0 °C

With titanium(IV) isopropylate; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; zinc(II) chloride; zinc; tert.-butylhydroperoxide; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 4.1: Swern oxidation / 7.1: Swern oxidation / 8.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2004.08.099

Reference yield:

(S)-3-Benzyloxy-pentan-1-ol (790699-41-1) → [(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-acetic acid methyl ester (790699-97-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

2.1: CH₂Cl₂ / 3 h / 0 - 20 °C

3.1: 62 percent / LiCl; NaBH₄ / ethanol; tetrahydrofuran / 72 h / 20 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

5.1: n-BuLi / tetrahydrofuran; CH₂Cl₂ / 0.5 h / -78 - 0 °C

5.2: tetrahydrofuran / 1 h / -78 - 0 °C

6.1: 62 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

7.1: Ti(OiPr)4; (+)-DIPT; 4A MS / TBHP / CH₂Cl₂ / 0.67 h / -23 °C

8.1: mCPBA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

9.1: 60 percent / Zn; ZnCl₂ / cp2TiCl₂ / tetrahydrofuran / 6 h / -20 - 20 °C

10.1: 94 percent / CSA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

11.1: 93 percent / TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

12.1: SO₃*py; Et₃N / dimethylsulfoxide / 1 h / 0 - 20 °C

12.2: NaClO₂; Na₂HPO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 1.5 h / 20 °C

13.1: diethyl ether / 0.25 h / 0 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium chloride; zinc(II) chloride; zinc; tert.-butylhydroperoxide; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; 1.1: Swern oxidation / 4.1: Swern oxidation / 5.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2004.08.099

upstream raw materials:

diazomethane

benzyl bromide

(S)-pentane-1,3-diol

(S)-3-Benzyloxy-pentan-1-ol

Downstream raw materials:

(4R,5S,6S)-6-((S)-4-Benzyloxy-hexyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-one

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