Hemibrevetoxin B

Base Information

• Chemical Name: Hemibrevetoxin B
• CAS No.: 122271-91-4
• Molecular Formula: C₂₈H₄₂O₇
• Molecular Weight: 490.637
• DSSTox Substance ID: DTXSID70880093
• Nikkaji Number: J640.611D
• Wikidata: Q82003369
• Metabolomics Workbench ID: 143756
• Mol file: 122271-91-4.mol

Synonyms:hemibrevetoxin B

Chemical Property of Hemibrevetoxin B

Chemical Property:

• Vapor Pressure: 5.78E-20mmHg at 25°C
• Boiling Point: 655.5°Cat760mmHg
• Flash Point: 211.9°C
• PSA: 94.45000
• Density: 1.104g/cm³
• LogP: 3.56620
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 490.29305367
• Heavy Atom Count: 35
• Complexity: 811

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(CCC(C(O3)CCC=CC=C)(C)O)OC1CC4C(O2)C(CC(O4)CC(=C)C=O)O
• Isomeric SMILES: C[C@@]12CC[C@H]3[C@@H](CC[C@]([C@H](O3)CC/C=C\C=C)(C)O)O[C@H]1C[C@@H]4[C@@H](O2)[C@H](C[C@H](O4)CC(=C)C=O)O

Technology Process of Hemibrevetoxin B

There total 97 articles about Hemibrevetoxin 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: 82.0%

oxepino<3,2-b>pyrano<2',3':5,6>pyrano<2,3-f>oxepin-2-propanal, 4,10-bis<(tert-butyldimethylsilyl)oxy>-9-(3,5-hexadienyl)hexadecahydro-5a,10-dimethyl-α-methylene-, <2R-<2α,4α,4aβ,5aβ,7aβ,9α(Z),10β,12aα,13aα,14aα>>- (147806-82-4,147853-15-4) → Hemibrevetoxin-B (122271-91-4)

Guidance literature:

With silicon tetrafluoride; In dichloromethane; acetonitrile; at 0 ℃; for 4h;

Reference yield:

((3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol (132375-56-5) → Hemibrevetoxin-B (122271-91-4)

Guidance literature:

Multi-step reaction with 48 steps

1: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

2: 98 percent / TFA / toluene / 0.25 h / 0 °C

3: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

4: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

6: benzene / 2 h / 80 °C

7: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

8: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

9: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

10: 1.) NaN(SiMe₃)2 / 1.) THF, 1 h, 2.) THF, 0 deg C, 30 min

11: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

12: 90 percent / CSA / CH₂Cl₂ / 5 h / 0 °C

13: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

14: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF, 1 h

15: 98 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

16: 89 percent / benzene / 3 h / 25 °C

17: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h

18: 92 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 50 °C

19: 95 percent / TBAF / tetrahydrofuran / 18 h / 25 °C

20: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

21: 82 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 3 h / 110 °C

22: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

23: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 30 min

24: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 25 °C

25: 95 percent / CSA / CH₂Cl₂; methanol / 0.5 h / Ambient temperature

26: 94 percent / PDC / dimethylformamide / 16 h / 25 °C

27: 100 percent / K₂CO₃ / methanol / 3 h / 25 °C

28: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

29: 75 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 5 h / 110 °C

30: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

31: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

32: 1.) oxalyl chloride, DMSO, 2.) DBU / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) toluene, 110 deg C, 2 h

33: 56 percent / diethyl ether / 4 h / -78 - -10 °C

34: 89 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4 h / 2068.6 Torr

35: 90 percent / 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1 h / Ambient temperature

36: 82 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 25 °C

37: 95 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

38: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

39: benzene / 3 h / 80 °C

40: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h

41: 86 percent / CSA / CH₂Cl₂; methanol / 3 h / 0 °C

42: 90 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

43: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, HMPA, from -78 deg C to RT, 30 min

44: NaHCO₃, 30percent aq

With Lawessons reagent; 1,2,2,6,6-pentamethylpiperidine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,4-Diiodobutane; dmap; lithium hydroxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; silicon tetrafluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

Reference yield:

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol (122821-81-2) → Hemibrevetoxin-B (122271-91-4)

Guidance literature:

Multi-step reaction with 49 steps

1: 80 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

2: 90 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / 25 °C

3: 98 percent / TFA / toluene / 0.25 h / 0 °C

4: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, 60 deg C, 1.5 h, 2.) DMF, 25 deg C, 16 h

5: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, 25 deg C, 1 h

7: benzene / 2 h / 80 °C

8: 85 percent / DIBAL / CH₂Cl₂ / 1 h / -78 °C

9: 97 percent / (+)-diethyl tartrate ((+)-DET), Ti(Oi-Pr)4, i-BuOOH, 4A molecular sieves / CH₂Cl₂ / 16 h / -20 °C

10: SO₃*pyridine, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

11: 1.) NaN(SiMe₃)2 / 1.) THF, 1 h, 2.) THF, 0 deg C, 30 min

12: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

13: 90 percent / CSA / CH₂Cl₂ / 5 h / 0 °C

14: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

15: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF, 1 h

16: 98 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

17: 89 percent / benzene / 3 h / 25 °C

18: 96 percent / H₂ / 5percent Pd/C / ethyl acetate / 15 h

19: 92 percent / LiOH / tetrahydrofuran; H₂O / 1 h / 50 °C

20: 95 percent / TBAF / tetrahydrofuran / 18 h / 25 °C

21: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

22: 82 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 3 h / 110 °C

23: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

24: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 30 min, 2.) THF, 0 deg C, 30 min

25: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 1 h / 25 °C

26: 95 percent / CSA / CH₂Cl₂; methanol / 0.5 h / Ambient temperature

27: 94 percent / PDC / dimethylformamide / 16 h / 25 °C

28: 100 percent / K₂CO₃ / methanol / 3 h / 25 °C

29: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) 4-(dimethylamino)pyridine (DMAP) / 1.) THF, RT, 2 h, 2.) THF, toluene, reflux, 1 h

30: 75 percent / 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide / toluene / 5 h / 110 °C

31: 1.) t-BuLi, 2.) (2-thienyl)cyanocopper lithium, 3.) 1,4-diiodobutane, pempidine

32: 1.) BH₃*THF, 2.) 3 N aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) THF

33: 1.) oxalyl chloride, DMSO, 2.) DBU / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) toluene, 110 deg C, 2 h

34: 56 percent / diethyl ether / 4 h / -78 - -10 °C

35: 89 percent / H₂ / Pd(OH)2/C / ethyl acetate / 4 h / 2068.6 Torr

36: 90 percent / 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1 h / Ambient temperature

37: 82 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 25 °C

38: 95 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

39: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

40: benzene / 3 h / 80 °C

41: 95 percent / H₂ / 5percent Pd/C / ethyl acetate / 16 h

42: 86 percent / CSA / CH₂Cl₂; methanol / 3 h / 0 °C

43: 90 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

44: 1.) n-BuLi / 1.) THF, -78 deg C, 15 min, 2.) THF, HMPA, from

With Lawessons reagent; 1,2,2,6,6-pentamethylpiperidine; 2,6-dimethylpyridine; titanium(IV) isopropylate; 1,4-Diiodobutane; dmap; lithium hydroxide; sodium hydroxide; dipyridinium dichromate; n-butyllithium; borane-THF; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; iso-butyl hydroperoxide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; tert.-butyl lithium; sodium hexamethyldisilazane; silicon tetrafluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; potassium carbonate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; thien-2-yl(cyano)copper lithium; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

upstream raw materials:

oxepino<3,2-b>pyrano<2',3':5,6>pyrano<2,3-f>oxepin-2-propanal, 4,10-bis<(tert-butyldimethylsilyl)oxy>-9-(3,5-hexadienyl)hexadecahydro-5a,10-dimethyl-α-methylene-, <2R-<2α,4α,4aβ,5aβ,7aβ,9α(Z),10β,12aα,13aα,14aα>>-

C₄₃H₇₆O₇Si₂

C₂₈H₄₄O₇

C₄₀H₇₆O₇Si₂

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