(2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione

Base Information

• Chemical Name: (2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione
• CAS No.: 147806-90-4
• Molecular Formula: C₂₈H₃₄O₅S
• Molecular Weight: 482.641
• Mol file: 147806-90-4.mol

Synonyms:(2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione

Chemical Property of (2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione

There total 27 articles about (2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione 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%

(2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-one (143293-33-8) → (2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione (147806-90-4)

Guidance literature:

With Lawessons reagent; In toluene; at 110 ℃; for 3h;

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) → (2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione (147806-90-4)

Guidance literature:

Multi-step reaction with 21 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

With Lawessons reagent; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; lithium hydroxide; sodium hydroxide; 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; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; 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) → (2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-thione (147806-90-4)

Guidance literature:

Multi-step reaction with 22 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

With Lawessons reagent; 2,6-dimethylpyridine; titanium(IV) isopropylate; dmap; lithium hydroxide; sodium hydroxide; 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; sodium hexamethyldisilazane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; benzene;

upstream raw materials:

(2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-one

benzyl bromide

((3aR,4R,6S,7aS)-4-Allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-methanol

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

Downstream raw materials:

[4-((2S,4S,4aS,5aR,10aS,11aR)-4-Benzyloxy-2-benzyloxymethyl-5a-methyl-2,3,4,4a,5a,6,7,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl)-butoxy]-tert-butyl-dimethyl-silane

Hemibrevetoxin-B

C₃₂H₄₀O₆S

C₃₂H₄₀O₇