3-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-Methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-propionitrile

Base Information

Chemical Name:3-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-Methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-propionitrile
CAS No.:195316-13-3
Molecular Formula:C₃₆H₄₁NO₇
Molecular Weight:599.724
Hs Code.:

Synonyms:3-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-Methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-propionitrile

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Chemical Property of 3-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-Methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-propionitrile

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Technology Process of 3-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-Methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-propionitrile

There total 40 articles about 3-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-Methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-propionitrile 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: 100.0%

: 143-33-9,25596-52-5
sodium cyanide

: 195316-43-9
Toluene-4-sulfonic acid 2-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-ethyl ester

: 195316-13-3
3-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-Methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-propionitrile

Guidance literature:: In dimethyl sulfoxide; at 60 ℃; for 3.3h;
DOI:10.1248/cpb.45.1265

Reference yield:

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

: 195316-13-3
3-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-Methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-propionitrile

Guidance literature:: Multi-step reaction with 35 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

32: 98 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

33: 100 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

34: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h

35: 100 percent / dimethylsulfoxide / 3.3 h / 60 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; 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:

: 195316-38-2
(2R,3R,4R,5R)-5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((4S,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methoxymethoxy-tetrahydro-furan-3-ol

: 195316-13-3
3-[(3aS,4S,5aR,6S,7R,8aR,8bR)-6-Methoxymethoxy-2,2-dimethyl-7-(2-trityloxy-ethyl)-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-4-yl]-propionitrile

Guidance literature:: Multi-step reaction with 11 steps

1: 97 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / Ambient temperature

2: 98 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

3: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

4: 100 percent / imidazole, DMAP / dimethylformamide / 15 h / 40 °C

5: 99 percent / DIBAH / CH₂Cl₂; hexane / 1.5 h / -78 °C

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

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

8: 98 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

9: 100 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

10: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h

11: 100 percent / dimethylsulfoxide / 3.3 h / 60 °C

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; oxalyl dichloride; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1248/cpb.45.1265