C₄₃H₅₂O₉

Base Information

• Chemical Name: C₄₃H₅₂O₉
• CAS No.: 259258-13-4
• Molecular Formula: C₄₃H₅₂O₉
• Molecular Weight: 712.88

Synonyms:

Chemical Property of C₄₃H₅₂O₉

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₄₃H₅₂O₉

There total 28 articles about C₄₃H₅₂O₉ 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) → C43H52O9 (259258-13-4)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 83 percent / sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 50 °C

2.1: 77 percent / dimethyl sulfide; BF₃*Et₂O / CH₂Cl₂ / 0.33 h / 0 °C

3.1: 93 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 2 h / 0 °C

4.1: 89 percent / dimethylsulfoxide / 5.5 h / 70 °C

5.1: DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

5.2: 80 percent / benzene / 1 h / 80 °C

6.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / 0 °C

7.1: 89 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

8.1: 75 percent / D-(-)-diethyl tartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

9.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

10.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

10.2: 1.081 g / tetrahydrofuran / 0.5 h / 0 °C

11.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

12.1: camphorsulfonic acid / CH₂Cl₂ / -40 - 0 °C

12.2: sodium hydride / dimethylformamide; various solvent(s) / 0 - 20 °C

13.1: N-methylmorpholine N-oxide; OsO₄ / H₂O; acetone / 20 °C

14.1: NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

15.1: 16.1 mg / benzene / 1 h / 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; pyridine-SO₃ complex; dimethylsulfide; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; benzene; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Tosylation / 4.1: Substitution / 5.1: Reduction / 5.2: Substitution / 6.1: Etherification / 7.1: Reduction / 8.1: Epoxidation / 9.1: Oxidation / 10.1: Dehydrobromination / 10.2: Substitution / 11.1: Hydrolysis / 12.1: Ring cleavage / 12.2: Methylation / 13.1: Oxidation / 14.1: Oxidation / 15.1: Substitution;

DOI:10.1021/jo990988j

Reference yield:

(2R,3R,4R)-5-Allyloxy-2-[(1S,2S)-1-benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-methyl-tetrahydro-furan-3-ol → C43H52O9 (259258-13-4)

Guidance literature:

Multi-step reaction with 27 steps

1.1: potassium dimsylate / tetrahydrofuran; dimethylsulfoxide / 0 - 20 °C

1.2: 16.64 g / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

2.1: [Ir(COD)(Ph₂MeP)2]PF₆; hydrogen / tetrahydrofuran / 0.58 h / 20 °C

2.2: 9.69 g / iodine / tetrahydrofuran; H₂O / 0.08 h / 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

3.2: 71 percent / tetrahydrofuran / 0 - 20 °C

4.1: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2.5 h / 20 °C

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C

5.2: 9.90 g / hydrogen peroxide; sodium hydroxide / tetrahydrofuran / 1.5 h / 20 °C

6.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

7.1: acetic acid / tetrahydrofuran; H₂O / 20 °C

8.1: 6.98 g / pyridinium dichromate; molecular sieves 4A / CH₂Cl₂ / 2 h / 20 °C

9.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: 92 percent / tetrahydrofuran; hexane / -78 - 0 °C

10.1: 79 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C

11.1: N,N'-bis(2,4,6-Me₃C₆H₂CH₂)-(S,S)-1,2-Ph₂-1,2-diaminoethane; osmium tetroxide / CH₂Cl₂ / 2 h / -90 °C

11.2: 85 percent / NaHSO₃ / tetrahydrofuran; H₂O / 2 h / Heating

12.1: 86 percent / camphorsulfonic acid / benzene / 36 h / 20 °C

13.1: 83 percent / sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 50 °C

14.1: 77 percent / dimethyl sulfide; BF₃*Et₂O / CH₂Cl₂ / 0.33 h / 0 °C

15.1: 93 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 2 h / 0 °C

16.1: 89 percent / dimethylsulfoxide / 5.5 h / 70 °C

17.1: DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

17.2: 80 percent / benzene / 1 h / 80 °C

18.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / 0 °C

19.1: 89 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

20.1: 75 percent / D-(-)-diethyl tartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

21.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

22.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

22.2: 1.081 g / tetrahydrofuran / 0.5 h / 0 °C

23.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

24.1: camphorsulfonic acid / CH₂Cl₂ / -40 - 0 °C

24.2: sodium hydride / dimethylformamide; various solvent(s) / 0 - 20 °C

25.1: N-methylmorpholine N-oxide; OsO₄ / H₂O; acetone / 20 °C

26.1: NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

27.1: 16.1 mg / benzene / 1 h / 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; pyridine-SO₃ complex; dimethylsulfide; diethyl (2S,3S)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; potassium dimsylate; sodium hydride; diisobutylaluminium hydride; acetic acid; 4-methylmorpholine N-oxide; (1S,2S)-1,2-diphenyl-N¹,N²-bis(mesitylmethyl)ethane-1,2-diamine; triethylamine; 9-bora-bicyclo[3.3.1]nonane; lithium hexamethyldisilazane; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; benzene; 1.1: Cyclization / 1.2: Etherification / 2.1: Hydrolysis / 2.2: Hydrolysis / 3.1: Dehydrobromination / 3.2: methylenation; Wittig reaction / 4.1: Addition / 5.1: hydroboration / 5.2: Oxidation / 6.1: Oxidation / 7.1: Hydrolysis / 8.1: Oxidation / 9.1: Metallation / 9.2: Methylation / 10.1: Addition / 11.1: Oxidation / 11.2: Ring cleavage / 12.1: Cyclization / 13.1: Etherification / 14.1: Hydrolysis / 15.1: Tosylation / 16.1: Substitution / 17.1: Reduction / 17.2: Substitution / 18.1: Etherificat;

DOI:10.1021/jo990988j

Reference yield:

(3R,3aR,5S,6R,7S,8S,8aS)-8-Benzyloxy-5-methoxymethoxymethyl-3,7-dimethyl-6-triisopropylsilanyloxy-octahydro-furo[3,2-b]oxepin-2-ol → C43H52O9 (259258-13-4)

Guidance literature:

Multi-step reaction with 25 steps

1.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

1.2: 71 percent / tetrahydrofuran / 0 - 20 °C

2.1: 98 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2.5 h / 20 °C

3.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C

3.2: 9.90 g / hydrogen peroxide; sodium hydroxide / tetrahydrofuran / 1.5 h / 20 °C

4.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

5.1: acetic acid / tetrahydrofuran; H₂O / 20 °C

6.1: 6.98 g / pyridinium dichromate; molecular sieves 4A / CH₂Cl₂ / 2 h / 20 °C

7.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 92 percent / tetrahydrofuran; hexane / -78 - 0 °C

8.1: 79 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C

9.1: N,N'-bis(2,4,6-Me₃C₆H₂CH₂)-(S,S)-1,2-Ph₂-1,2-diaminoethane; osmium tetroxide / CH₂Cl₂ / 2 h / -90 °C

9.2: 85 percent / NaHSO₃ / tetrahydrofuran; H₂O / 2 h / Heating

10.1: 86 percent / camphorsulfonic acid / benzene / 36 h / 20 °C

11.1: 83 percent / sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 50 °C

12.1: 77 percent / dimethyl sulfide; BF₃*Et₂O / CH₂Cl₂ / 0.33 h / 0 °C

13.1: 93 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 2 h / 0 °C

14.1: 89 percent / dimethylsulfoxide / 5.5 h / 70 °C

15.1: DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

15.2: 80 percent / benzene / 1 h / 80 °C

16.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / 0 °C

17.1: 89 percent / DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

18.1: 75 percent / D-(-)-diethyl tartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

19.1: triethylamine; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

20.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C

20.2: 1.081 g / tetrahydrofuran / 0.5 h / 0 °C

21.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

22.1: camphorsulfonic acid / CH₂Cl₂ / -40 - 0 °C

22.2: sodium hydride / dimethylformamide; various solvent(s) / 0 - 20 °C

23.1: N-methylmorpholine N-oxide; OsO₄ / H₂O; acetone / 20 °C

24.1: NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

25.1: 16.1 mg / benzene / 1 h / 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; pyridine-SO₃ complex; dimethylsulfide; diethyl (2S,3S)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; acetic acid; 4-methylmorpholine N-oxide; (1S,2S)-1,2-diphenyl-N¹,N²-bis(mesitylmethyl)ethane-1,2-diamine; triethylamine; 9-bora-bicyclo[3.3.1]nonane; lithium hexamethyldisilazane; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; benzene; 1.1: Dehydrobromination / 1.2: methylenation; Wittig reaction / 2.1: Addition / 3.1: hydroboration / 3.2: Oxidation / 4.1: Oxidation / 5.1: Hydrolysis / 6.1: Oxidation / 7.1: Metallation / 7.2: Methylation / 8.1: Addition / 9.1: Oxidation / 9.2: Ring cleavage / 10.1: Cyclization / 11.1: Etherification / 12.1: Hydrolysis / 13.1: Tosylation / 14.1: Substitution / 15.1: Reduction / 15.2: Substitution / 16.1: Etherification / 17.1: Reduction / 18.1: Epoxidation / 19.1: Oxidation / 20.1: Dehydrobromi;

DOI:10.1021/jo990988j

upstream raw materials:

(carbobenzyloxymethylene)triphenylphosphorane

benzyl bromide

(2R,3S,4S,5S,6R,7S)-4-Benzyloxy-7-methoxymethoxymethyl-5-methyl-2-((S)-1-methyl-allyl)-6-triisopropylsilanyloxy-oxepan-3-ol

(4S,4aR,6S,7R,8S,9S,9aS)-9-Benzyloxy-6-methoxymethoxymethyl-4,8-dimethyl-7-triisopropylsilanyloxy-octahydro-1,5-dioxa-benzocyclohepten-2-one

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