C₃₃H₄₈O₉

Base Information

• Chemical Name: C₃₃H₄₈O₉
• CAS No.: 474125-38-7
• Molecular Formula: C₃₃H₄₈O₉
• Molecular Weight: 588.739

Synonyms:C₃₃H₄₈O₉

Chemical Property of C₃₃H₄₈O₉

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₃₃H₄₈O₉

There total 23 articles about C₃₃H₄₈O₉ 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:

(3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one (196393-04-1) → C33H48O9 (474125-38-7)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 95 percent / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 24 h / 50 °C

2.1: tetrahydrofuran / 1.17 h / -70 °C

3.1: disiamylborane / tetrahydrofuran / 1.17 h / 0 °C

3.2: H₂O₂; NaHCO₃ / tetrahydrofuran; methanol; H₂O / 20 °C

4.1: 37.5 g / 10-camphorsulfonic acid / 1,2-dichloro-ethane / 3 h / 20 °C

5.1: 100 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 24 h / 20 °C

6.1: DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 2.25 h / -80 - -60 °C

7.1: 4.8 g / toluene / 0.58 h / -80 - -70 °C

8.1: 3.79 g / NaH / tetrahydrofuran; dimethylformamide / 7 h / 20 °C

9.1: N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 20 °C

10.1: NaIO₄ / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

11.1: 437 mg / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

12.1: 75 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine; 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 35 °C

13.1: 63 percent / tetrahydrofuran / 60 °C

14.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

14.2: 75 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

15.1: 57 percent / DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 1.5 h / -70 - -40 °C

16.1: 58 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 12 h / 20 °C

17.1: 84 percent / trifluoromethanesulfonic acid / hexane / 19 h / 20 °C

18.1: 71 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -50 - -20 °C

19.1: 99 percent / hydrogen; AcOH / Pd(OH)2/C / ethyl acetate; methanol / 72 h / 20 °C

20.1: 174 mg / 10-camphorsulfonic acid / tetrahydrofuran / 1 h / 20 °C

With triethylsilane; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; hydrogen; bis-(1,2-dimethylpropyl)borane; sodium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 6.1: Swern oxidation / 15.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)00660-9

Reference yield:

(E)-(R)-6-Benzyloxy-2,3-dimethyl-hex-4-enoic acid → C33H48O9 (474125-38-7)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 24.8 g / ethyl acetate / 0 - 20 °C

2.1: 62 percent / I₂ / acetonitrile / 0 - 20 °C

3.1: aq. NaOH / ethanol / 2 h / 20 °C

3.2: 72 percent / AcOH / ethanol / 1 h / 60 °C

4.1: 95 percent / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 24 h / 50 °C

5.1: tetrahydrofuran / 1.17 h / -70 °C

6.1: disiamylborane / tetrahydrofuran / 1.17 h / 0 °C

6.2: H₂O₂; NaHCO₃ / tetrahydrofuran; methanol; H₂O / 20 °C

7.1: 37.5 g / 10-camphorsulfonic acid / 1,2-dichloro-ethane / 3 h / 20 °C

8.1: 100 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 24 h / 20 °C

9.1: DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 2.25 h / -80 - -60 °C

10.1: 4.8 g / toluene / 0.58 h / -80 - -70 °C

11.1: 3.79 g / NaH / tetrahydrofuran; dimethylformamide / 7 h / 20 °C

12.1: N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 20 °C

13.1: NaIO₄ / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

14.1: 437 mg / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

15.1: 75 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine; 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 35 °C

16.1: 63 percent / tetrahydrofuran / 60 °C

17.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

17.2: 75 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

18.1: 57 percent / DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 1.5 h / -70 - -40 °C

19.1: 58 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 12 h / 20 °C

20.1: 84 percent / trifluoromethanesulfonic acid / hexane / 19 h / 20 °C

21.1: 71 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -50 - -20 °C

22.1: 99 percent / hydrogen; AcOH / Pd(OH)2/C / ethyl acetate; methanol / 72 h / 20 °C

23.1: 174 mg / 10-camphorsulfonic acid / tetrahydrofuran / 1 h / 20 °C

With triethylsilane; dmap; sodium hydroxide; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; hydrogen; iodine; bis-(1,2-dimethylpropyl)borane; sodium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 9.1: Swern oxidation / 18.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)00660-9

Reference yield:

(3S,4S,5S)-5-((R)-2-Benzyloxy-1-iodo-ethyl)-3,4-dimethyl-dihydro-furan-2-one (196392-89-9) → C33H48O9 (474125-38-7)

Guidance literature:

Multi-step reaction with 21 steps

1.1: aq. NaOH / ethanol / 2 h / 20 °C

1.2: 72 percent / AcOH / ethanol / 1 h / 60 °C

2.1: 95 percent / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 24 h / 50 °C

3.1: tetrahydrofuran / 1.17 h / -70 °C

4.1: disiamylborane / tetrahydrofuran / 1.17 h / 0 °C

4.2: H₂O₂; NaHCO₃ / tetrahydrofuran; methanol; H₂O / 20 °C

5.1: 37.5 g / 10-camphorsulfonic acid / 1,2-dichloro-ethane / 3 h / 20 °C

6.1: 100 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 24 h / 20 °C

7.1: DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 2.25 h / -80 - -60 °C

8.1: 4.8 g / toluene / 0.58 h / -80 - -70 °C

9.1: 3.79 g / NaH / tetrahydrofuran; dimethylformamide / 7 h / 20 °C

10.1: N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 20 °C

11.1: NaIO₄ / 2-methyl-propan-2-ol; H₂O / 1 h / 20 °C

12.1: 437 mg / NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

13.1: 75 percent / 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine; 10-camphorsulfonic acid / CH₂Cl₂ / 24 h / 35 °C

14.1: 63 percent / tetrahydrofuran / 60 °C

15.1: BH₃*THF / tetrahydrofuran / 0 - 20 °C

15.2: 75 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

16.1: 57 percent / DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 1.5 h / -70 - -40 °C

17.1: 58 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 12 h / 20 °C

18.1: 84 percent / trifluoromethanesulfonic acid / hexane / 19 h / 20 °C

19.1: 71 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -50 - -20 °C

20.1: 99 percent / hydrogen; AcOH / Pd(OH)2/C / ethyl acetate; methanol / 72 h / 20 °C

21.1: 174 mg / 10-camphorsulfonic acid / tetrahydrofuran / 1 h / 20 °C

With triethylsilane; dmap; sodium hydroxide; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; hydrogen; bis-(1,2-dimethylpropyl)borane; sodium hydride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 7.1: Swern oxidation / 16.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)00660-9

upstream raw materials:

p-Anisaldehyde dimethyl acetal

C₂₅H₄₂O₈

(3S,4S,5R,6S)-6-Benzyloxymethyl-5-hydroxy-3,4-dimethyl-tetrahydro-pyran-2-one

(3S,4S,5S)-5-((R)-2-Benzyloxy-1-iodo-ethyl)-3,4-dimethyl-dihydro-furan-2-one

Downstream raw materials:

C₄₁H₅₆O₁₀

C₄₇H₆₆O₁₁

C₄₅H₆₄O₁₁

C₄₆H₆₄O₁₀

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