(E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester

Base Information

Chemical Name:(E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester
CAS No.:195316-11-1
Molecular Formula:C₄₃H₅₈O₉Si
Molecular Weight:747.014
Hs Code.:

(E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester

Synonyms:(E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester

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Chemical Property of (E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester

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Technology Process of (E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester

There total 33 articles about (E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester 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:

: 155369-79-2
(2R,3R,4S,5R)-4-Benzyloxy-5-[1,3]dithian-2-yl-2-hydroxymethyl-tetrahydro-furan-3-ol

: 195316-11-1
(E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 31 steps

1: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

2: 1.) NaH / 1.) THF, DMSO, RT, 2.) THF, DMSO, RT, 3 h

3: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

4: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

5: HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 1.5 h / 60 °C

6: 1.) tert-BuOK / 1.) THF, RT, 30 min, 2.) THF, 30 min

7: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

8: 1.) D-(-)-diethyl tartrate, Ti(O-iPr)4, 4 Angstroem molecular sieves, 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, -20 deg C, 30 min, 2.) CH₂Cl₂, 2,2,4-trimethylpentane, 3 d

9: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

10: BF₃*Et₂O / diethyl ether / 2 h / 0 °C

11: 96 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

12: 88 percent / DMAP, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

13: 100 percent / PPTS / CH₂Cl₂ / 2 h / Ambient temperature

14: 89 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

15: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 °C

16: 96 percent / dimethylsulfoxide / 5 h / 80 °C

17: DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

18: NaBH₄ / tetrahydrofuran; methanol / 4 h / Ambient temperature

19: 100 percent / imidazole / CH₂Cl₂ / 1.5 h / Ambient temperature

20: 95 percent / DDQ, phosphate buffer / CH₂Cl₂ / 1 h / Ambient temperature

21: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 1 h

22: NaBH₄ / tetrahydrofuran; methanol / 1.5 h / -78 °C

23: 97 percent / diisopropylethylamine, DMAP / CH₂Cl₂ / 33 h / 40 °C

24: 94 percent / Na, liq. NH₃ / tetrahydrofuran / 0.5 h / -78 °C

25: 97 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / Ambient temperature

26: 98 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

27: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

28: 100 percent / imidazole, DMAP / dimethylformamide / 15 h / 40 °C

29: 99 percent / DIBAH / CH₂Cl₂; hexane / 1.5 h / -78 °C

30: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -40 deg C, 20 min

31: 1.) tert-BuOK / 1.) THF, 0 deg C, 20 min, 2.) THF, -78 deg C, 40 min

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; phosphate buffer; oxalyl dichloride; diethyl (2S,3S)-tartrate; DL-10-camphorsulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; sodium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1248/cpb.45.1265

Reference yield:

: 195316-09-7
2,2-Dimethyl-propionic acid (4S,5S)-5-[(2R,3R,4R,5R)-3-hydroxy-5-(2-hydroxy-ethyl)-4-methoxymethoxy-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 195316-11-1
(E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

2: 100 percent / imidazole, DMAP / dimethylformamide / 15 h / 40 °C

3: 99 percent / DIBAH / CH₂Cl₂; hexane / 1.5 h / -78 °C

4: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -40 deg C, 20 min

5: 1.) tert-BuOK / 1.) THF, 0 deg C, 20 min, 2.) THF, -78 deg C, 40 min

With 1H-imidazole; dmap; oxalyl dichloride; potassium tert-butylate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.45.1265

Reference yield:

: 195315-83-4
6-O-benzoyl-3-O-benzyl-D-glucose propylene dithioacetal

: 195316-11-1
(E)-3-{(4S,5S)-5-[(2S,3R,4S,5R)-4-Methoxymethoxy-3-triethylsilanyloxy-5-(2-trityloxy-ethyl)-tetrahydro-furan-2-yl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acrylic acid ethyl ester

Guidance literature:: Multi-step reaction with 36 steps

1: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

2: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

3: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

4: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

5: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

6: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

7: 1.) NaH / 1.) THF, DMSO, RT, 2.) THF, DMSO, RT, 3 h

8: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

9: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

10: HgO, BF₃*Et₂O / tetrahydrofuran; H₂O / 1.5 h / 60 °C

11: 1.) tert-BuOK / 1.) THF, RT, 30 min, 2.) THF, 30 min

12: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

13: 1.) D-(-)-diethyl tartrate, Ti(O-iPr)4, 4 Angstroem molecular sieves, 2.) tert-butyl hydroperoxide / 1.) CH₂Cl₂, -20 deg C, 30 min, 2.) CH₂Cl₂, 2,2,4-trimethylpentane, 3 d

14: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

15: BF₃*Et₂O / diethyl ether / 2 h / 0 °C

16: 96 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

17: 88 percent / DMAP, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

18: 100 percent / PPTS / CH₂Cl₂ / 2 h / Ambient temperature

19: 89 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

20: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 °C

21: 96 percent / dimethylsulfoxide / 5 h / 80 °C

22: DIBAH / CH₂Cl₂; hexane / 1 h / -78 °C

23: NaBH₄ / tetrahydrofuran; methanol / 4 h / Ambient temperature

24: 100 percent / imidazole / CH₂Cl₂ / 1.5 h / Ambient temperature

25: 95 percent / DDQ, phosphate buffer / CH₂Cl₂ / 1 h / Ambient temperature

26: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -60 deg C, 1 h

27: NaBH₄ / tetrahydrofuran; methanol / 1.5 h / -78 °C

28: 97 percent / diisopropylethylamine, DMAP / CH₂Cl₂ / 33 h / 40 °C

29: 94 percent / Na, liq. NH₃ / tetrahydrofuran / 0.5 h / -78 °C

30: 97 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / Ambient temperature

31: 98 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

32: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

33: 100 percent / imidazole, DMAP / dimethylformamide / 15 h / 40 °C

34: 99 percent / DIBAH / CH₂Cl₂; hexane / 1.5 h / -78 °C

35: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, -40 deg C, 20 min

36: 1.) tert-BuOK / 1.) THF, 0 deg C, 20 min, 2.) THF, -78 deg C, 40 min

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; phosphate buffer; oxalyl dichloride; diethyl (2S,3S)-tartrate; DL-10-camphorsulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; sodium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1248/cpb.45.1265