2-[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanol

Base Information

• Chemical Name: 2-[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanol
• CAS No.: 790699-95-5
• Molecular Formula: C₂₂H₃₆O₄
• Molecular Weight: 364.525
• Mol file: 790699-95-5.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about 2-[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanol 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) → 2-[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanol (790699-95-5)

Guidance literature:

Multi-step reaction with 13 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

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 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; ethanol; dichloromethane; 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)-3-(phenylmethoxy)-1-pentanal (153077-77-1) → 2-[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanol (790699-95-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: CH₂Cl₂ / 3 h / 0 - 20 °C

2.1: 62 percent / LiCl; NaBH₄ / ethanol; tetrahydrofuran / 72 h / 20 °C

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

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

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

5.1: 62 percent / NaBH₄ / methanol / 2 h / 0 - 20 °C

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

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

8.1: 60 percent / Zn; ZnCl₂ / cp2TiCl₂ / tetrahydrofuran / 6 h / -20 - 20 °C

9.1: 94 percent / CSA / CH₂Cl₂ / 0.75 h / 0 - 20 °C

10.1: 93 percent / TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 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; ethanol; dichloromethane; 3.1: Swern oxidation / 4.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2004.08.099

Reference yield:

(S)-3-Benzyloxy-pentan-1-ol (790699-41-1) → 2-[(4R,5R,6S)-6-((S)-4-Benzyloxy-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanol (790699-95-5)

Guidance literature:

Multi-step reaction with 11 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

With titanium(IV) isopropylate; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 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; ethanol; dichloromethane; 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:

benzyl bromide

(S)-3-(phenylmethoxy)-1-pentanal

(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

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