(2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol

Base Information

• Chemical Name: (2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol
• CAS No.: 944740-67-4
• Molecular Formula: C₂₂H₃₄O₄S₂
• Molecular Weight: 426.642
• Mol file: 944740-67-4.mol

Synonyms:(2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol

Chemical Property of (2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol

There total 1 articles about (2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol 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: 85.0%

1-methoxy-4-(methoxymethyl)benzene (1515-81-7) + (2S,3R,4R,6R)-6-(2-Ethyl-[1,3]dithiolan-2-yl)-2,4-dimethyl-heptane-1,3,4-triol → (2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol (944740-67-4)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2007.02.044

Reference yield: 91.0%

(2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol (944740-67-4) + t-butyldimethylsiyl triflate (69739-34-0) → (2S,3R,4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonane (944740-59-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1016/j.tet.2007.02.044

Reference yield:

(2S,3R,4R,6R)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol (944740-67-4) → C47H75NO13

Guidance literature:

Multi-step reaction with 39 steps

1.1: 91 percent / diisopropylethylamine / CH₂Cl₂ / 18 h / 20 °C

2.1: 96 percent / BH₃*THF; AlCl₃ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

3.1: 99 percent / ethyldiisopropylamine / CH₂Cl₂ / 1 h / 0 °C

4.1: 85 percent / CaCO₃; Hg(ClO₄)2 / tetrahydrofuran; H₂O / 0.25 h / 20 °C

5.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 - -15 °C

5.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

6.1: 73 percent / acetic acid; Me₄NBH₄ / acetonitrile / 70 h / -10 - -6 °C

7.1: 83 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

8.1: 88 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 40 h / 20 °C

9.1: 96 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; pyridine / CH₂Cl₂ / 2 h / 20 °C

10.1: 69 percent / BF₃*OEt₂ / CH₂Cl₂ / 5 h / -78 °C

11.1: 91 percent / molecular sieves 3 Angstroem; DDQ / CH₂Cl₂ / 0.5 h / 20 °C

12.1: ozone; pyridine; Sudan III / CH₂Cl₂ / -78 °C

12.2: 85 percent / triphenylphosphine / CH₂Cl₂ / 2 h / 20 °C

13.1: 100 percent / Na₂HPO₄; m-CPBA / tetrahydrofuran; H₂O / 15 h / 20 °C

14.1: 99 percent / hydrogen / palladium on charcoal / methanol; tetrahydrofuran / 3.5 h / 20 °C

15.1: 93 percent / 4-dimethylaminopyridine; triethylamine; 2,3,4-trichlorobenzoyl chloride / toluene / 0.25 h / 20 °C

16.1: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 28 h / 60 °C

17.1: 70 percent / KH₂PO₄; aq. HCl / tetrahydrofuran / 14 h / 50 °C

18.1: 61 percent / silver triflate; molecular sieves 4 Angstroem / CH₂Cl₂; toluene / 1 h / 0 °C

19.1: 40 percent / copper(II) oxide; molecular sieves 4 Angstroem; copper(II) trifluoromethanesulfonate / acetonitrile / 2 h / 20 °C

20.1: acetic acid; water / 14 h / 35 °C

21.1: 8.7 mg / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

22.1: 90 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 14 h / 20 °C

23.1: 95 percent / aq. MeOH / 8 h / Heating

24.1: 96 percent / I₂ / methanol / 20 °C / Irradiation

25.1: 95 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

26.1: 84 percent / NaBH₄ / 1,2-dimethoxy-ethane / 0 °C

27.1: 75 percent / PPTS / CH₂Cl₂ / 20 °C

28.1: 93 percent / H₂ / Pd/C / ethanol / 20 °C

29.1: 88 percent / LiAlH₄ / tetrahydrofuran / 0 - 20 °C

30.1: 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

30.2: NaH / tetrahydrofuran / 0 °C

31.1: 84 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 20 °C

32.1: 91 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

33.1: 86 percent / triethylamine / CH₂Cl₂ / 0 °C

34.1: 93 percent / KH; 18-crown-6 / tetrahydrofuran / 0 - 20 °C

35.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 20 °C

36.1: 82 percent / PDC / CH₂Cl₂ / 20 °C

37.1: 73 percent / NaClO₂; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

38.1: 76 percent / tetrabutylammonium fluoride / hexamethylphosphoric acid triamide / 80 °C

39.1: 53 percent / Cl₃C₆H₃COCl; triethylamine; 4-(dimethylamino)pyridine / tetrahydrofuran / Heating

With pyridine; hydrogenchloride; methanol; dmap; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; potassium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; aluminium trichloride; mercury(II) perchlorate; borane-THF; 2-methyl-but-2-ene; 18-crown-6 ether; oil scarlet; 3 A molecular sieve; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; iodine; silver trifluoromethanesulfonate; tetramethylammonium borohydride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; copper(II) bis(trifluoromethanesulfonate); sodium hydride; Dess-Martin periodane; ozone; acetic acid; (+)-10-camphorsulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate; copper(II) oxide; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 9.1: Dess-Martin oxidation / 15.1: Yamaguchi lactonization / 22.1: Dess-Martin oxidation / 39.1: Yamaguchi lactonization;

DOI:10.1016/j.tet.2007.02.044

upstream raw materials:

1-methoxy-4-(methoxymethyl)benzene

Downstream raw materials:

(2S,3R,4R,6R)-4-[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonane

(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

(2S,3R,4R,6R,7S,8S,9R,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecane-7,9-diol

(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-4-[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecanol

Refernces