Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl ester

Base Information

• Chemical Name: Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl ester
• CAS No.: 286958-18-7
• Molecular Formula: C₁₉H₂₄O₄
• Molecular Weight: 316.397
• Mol file: 286958-18-7.mol

Synonyms:Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl ester

Chemical Property of Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl ester

There total 14 articles about Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl 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: 60.0%

Benzoic acid (S)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-ethyl ester (286958-16-5) → Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl ester (286958-18-7)

Guidance literature:

Benzoic acid (S)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-ethyl ester; With 1H-imidazole; iodine; triphenylphosphine; In toluene; for 39.5h; Heating;

With ammonium chloride; zinc; In ethanol; at 26 ℃; for 6h;

DOI:10.1246/cl.2000.610

Reference yield:

(2S,3R)-2-(2-propenyl)-3-hydroxyoxane (242808-58-8) → Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl ester (286958-18-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: i-Pr₂NEt

2.1: OsO₄; NMO

3.1: NaIO₄

4.1: NaBH₄

5.1: t-BuOK; TBAI

6.1: 6M HCl / tetrahydrofuran

7.1: 99 percent / DCC; DMAP / CH₂Cl₂ / 22 - 24 °C

8.1: Cp₂TiCl₂ / toluene / 72 h / 23 °C

8.2: 97 percent / tetrahydrofuran; toluene / 0 - 23 °C

9.1: BH₃*THF / tetrahydrofuran / 0.67 h / 0 °C

9.2: 79 percent / 5M NaOH; 30 percent H₂O₂ / 13 h / 0 - 22 °C

10.1: DMAP / pyridine / 3.5 h / 25 °C

11.1: H₂ / Pd/C / ethanol / 22 - 25 °C

12.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.92 h / -78 - 0 °C

13.1: tetrahydrofuran / -78 - 0 °C

14.1: PPh₃; I₂; imidazole / toluene / 39.5 h / Heating

14.2: 60 percent / Zn; NH₄Cl / aq. ethanol / 6 h / 26 °C

With 1H-imidazole; hydrogenchloride; dmap; bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; borane-THF; oxalyl dichloride; potassium tert-butylate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; toluene; 1.1: Etherification / 2.1: dihydroxylation / 3.1: oxidative cleavage / 4.1: Reduction / 5.1: Etherification / 6.1: Hydrolysis / 7.1: Esterification / 8.1: complex formation / 8.2: olefination / 9.1: hydroboration / 9.2: Oxidation / 10.1: Esterification / 11.1: debenzylation / 12.1: Oxidation / 13.1: Wittig reaction / 14.1: Iodination / 14.2: Elimination;

DOI:10.1246/cl.2000.610

Reference yield:

(2S,3R)-2-Allyl-3-methoxymethoxy-tetrahydro-pyran → Benzoic acid (R)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-but-3-enyl ester (286958-18-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: OsO₄; NMO

2.1: NaIO₄

3.1: NaBH₄

4.1: t-BuOK; TBAI

5.1: 6M HCl / tetrahydrofuran

6.1: 99 percent / DCC; DMAP / CH₂Cl₂ / 22 - 24 °C

7.1: Cp₂TiCl₂ / toluene / 72 h / 23 °C

7.2: 97 percent / tetrahydrofuran; toluene / 0 - 23 °C

8.1: BH₃*THF / tetrahydrofuran / 0.67 h / 0 °C

8.2: 79 percent / 5M NaOH; 30 percent H₂O₂ / 13 h / 0 - 22 °C

9.1: DMAP / pyridine / 3.5 h / 25 °C

10.1: H₂ / Pd/C / ethanol / 22 - 25 °C

11.1: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.92 h / -78 - 0 °C

12.1: tetrahydrofuran / -78 - 0 °C

13.1: PPh₃; I₂; imidazole / toluene / 39.5 h / Heating

13.2: 60 percent / Zn; NH₄Cl / aq. ethanol / 6 h / 26 °C

With 1H-imidazole; hydrogenchloride; dmap; bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; borane-THF; oxalyl dichloride; potassium tert-butylate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; dichloromethane; toluene; 1.1: dihydroxylation / 2.1: oxidative cleavage / 3.1: Reduction / 4.1: Etherification / 5.1: Hydrolysis / 6.1: Esterification / 7.1: complex formation / 7.2: olefination / 8.1: hydroboration / 8.2: Oxidation / 9.1: Esterification / 10.1: debenzylation / 11.1: Oxidation / 12.1: Wittig reaction / 13.1: Iodination / 13.2: Elimination;

DOI:10.1246/cl.2000.610

upstream raw materials:

Benzoic acid (S)-2-((2S,3R)-2-allyl-tetrahydro-pyran-3-yloxy)-2-(S)-1,4-dioxa-spiro[4.5]dec-2-yl-ethyl ester

(2S,3R)-2-(2-propenyl)-3-hydroxyoxane

(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-ol

(S)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester