cinatrin B

Base Information

• Chemical Name: cinatrin B
• CAS No.: 136266-34-7
• Molecular Formula: C₁₈H₂₈O₈
• Molecular Weight: 372.416
• Mol file: 136266-34-7.mol

Synonyms:1,7-Dioxaspiro[4.4]nonane-4-carboxylicacid, 8-decyl-3,4-dihydroxy-2,6-dioxo-, [3R-[3a,4b,5b(R*)]]-; Cinatrin B

Chemical Property of cinatrin B

Chemical Property:

• Vapor Pressure: 1.34E-16mmHg at 25°C
• Boiling Point: 594.3°Cat760mmHg
• Flash Point: 210.2°C
• PSA: 130.36000
• Density: 1.3g/cm³
• LogP: 1.30490

Purity/Quality:

CINATRIN B 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of cinatrin B

There total 17 articles about cinatrin B 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: 30.0%

(-)-cinatrin B methyl ester (405145-26-8) → (-)-cinatrin B (136266-34-7)

Guidance literature:

(-)-cinatrin B methyl ester; With sodium hydroxide; In tetrahydrofuran; at 40 ℃; for 24h;

With hydrogenchloride; for 4.5h; Further stages.;

DOI:10.1021/jo016221k

Reference yield:

(2S,3S,4S,5R,8R)-3,4-Bis-benzyloxy-8-((R)-1-iodo-decyl)-2-methoxy-1,7-dioxa-spiro[4.4]nonan-6-one (404935-60-0) → (-)-cinatrin B (136266-34-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 94 percent / Bu₃SnH; AIBN / toluene / 1 h / 45 - 60 °C

2.1: 88 percent / H₂; aq. HCl / Pd(OH)2/C / methanol / 17 h / 3102.97 Torr

3.1: 88 percent / imidazole / dimethylformamide / 15 h / 20 °C

4.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 20 °C

5.1: 126 mg / aq. HF / acetonitrile / 4 h / 20 °C

6.1: EtMgBr / tetrahydrofuran / 0.67 h / 0 - 30 °C

6.2: 81 mg / tetrahydrofuran / 2.25 h / -78 - 0 °C

7.1: 61 percent / TBAF*3H₂O / tetrahydrofuran / 0.33 h

8.1: 83 percent / H₂ / Lindlar catalyst / methanol / 2 h

9.1: O₃ / CH₂Cl₂; methanol / -78 °C

9.2: Me₂S / methanol; CH₂Cl₂ / 0.5 h / -78 - 20 °C

10.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; H₂O / 17 h / 20 °C

11.1: aq. HCl; aq. AcOH / 3.5 h / 100 °C

12.1: 7.8 mg / I₂; CaCO₃ / methanol; H₂O / 18 h / 70 °C

13.1: aq. NaOH / tetrahydrofuran / 24 h / 40 °C

13.2: 30 percent / aq. HCl / 4.5 h

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; iodine; tri-n-butyl-tin hydride; Dess-Martin periodane; ozone; acetic acid; calcium carbonate; palladium dihydroxide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 4.1: Dess-Martin oxidation;

DOI:10.1021/jo016221k

Reference yield:

(2S,3R,5R,8S)-8-Decyl-3-hydroxy-2-methoxy-1,7-dioxa-spiro[4.4]nonane-4,6-dione (404935-55-3) → (-)-cinatrin B (136266-34-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: EtMgBr / tetrahydrofuran / 0.67 h / 0 - 30 °C

1.2: 81 mg / tetrahydrofuran / 2.25 h / -78 - 0 °C

2.1: 61 percent / TBAF*3H₂O / tetrahydrofuran / 0.33 h

3.1: 83 percent / H₂ / Lindlar catalyst / methanol / 2 h

4.1: O₃ / CH₂Cl₂; methanol / -78 °C

4.2: Me₂S / methanol; CH₂Cl₂ / 0.5 h / -78 - 20 °C

5.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; H₂O / 17 h / 20 °C

6.1: aq. HCl; aq. AcOH / 3.5 h / 100 °C

7.1: 7.8 mg / I₂; CaCO₃ / methanol; H₂O / 18 h / 70 °C

8.1: aq. NaOH / tetrahydrofuran / 24 h / 40 °C

8.2: 30 percent / aq. HCl / 4.5 h

With hydrogenchloride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; iodine; ozone; acetic acid; calcium carbonate; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo016221k

upstream raw materials:

(-)-cinatrin B methyl ester

(2S,3S,4S,5R,8R)-3,4-Bis-benzyloxy-8-((R)-1-iodo-decyl)-2-methoxy-1,7-dioxa-spiro[4.4]nonan-6-one

(2S,3R,5R,8S)-8-Decyl-3-hydroxy-2-methoxy-1,7-dioxa-spiro[4.4]nonane-4,6-dione

(2S,3S,4S,5R,8S)-8-Decyl-3,4-dihydroxy-2-methoxy-1,7-dioxa-spiro[4.4]nonan-6-one

Refernces