{2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Base Information

Chemical Name:{2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane
CAS No.:195316-37-1
Molecular Formula:C₄₆H₆₀O₈Si
Molecular Weight:769.063
Hs Code.:

{2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Synonyms:{2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

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Chemical Property of {2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

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Technology Process of {2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

There total 31 articles about {2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane 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: 97.0%

: 107-30-2
chloromethyl methyl ether

: 195316-08-6
(2R,3S,4S,5R)-4-Benzyloxy-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-ol

: 195316-37-1
{2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 40 ℃; for 33h;
DOI:10.1248/cpb.45.1265

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 195316-37-1
{2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 31 steps

1: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

3: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

4: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

5: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

6: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

7: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

8: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

9: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

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

11: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

12: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

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

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

15: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

16: 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

17: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

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

19: 96 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

20: 88 percent / DMAP, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

21: 100 percent / PPTS / CH₂Cl₂ / 2 h / Ambient temperature

22: 89 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

23: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 °C

24: 96 percent / dimethylsulfoxide / 5 h / 80 °C

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

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

27: 100 percent / imidazole / CH₂Cl₂ / 1.5 h / Ambient temperature

28: 95 percent / DDQ, phosphate buffer / CH₂Cl₂ / 1 h / Ambient temperature

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

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

31: 97 percent / diisopropylethylamine, DMAP / CH₂Cl₂ / 33 h / 40 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; 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; 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; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1248/cpb.45.1265

Reference yield:

: 37776-15-1
6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

: 195316-37-1
{2-[(2R,3S,4R,5R)-4-Benzyloxy-5-((4S,5S)-2,2-dimethyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-3-methoxymethoxy-tetrahydro-furan-2-yl]-ethoxy}-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 30 steps

1: 76 percent / 6 N aq. HCl / tetrahydrofuran / 5 h / Heating

2: 55 percent / ZnCl₂ / acetonitrile / 6.5 h / 60 °C

3: 85 percent / dl-CSA / CH₂Cl₂ / 1 h / Ambient temperature

4: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h

5: 97 percent / K₂CO₃ / methanol; CH₂Cl₂ / 1 h / 0 °C

6: 87 percent / t-BuOK / tetrahydrofuran / 0.5 h / Ambient temperature

7: 84 percent / 80percent AcOH / CH₂Cl₂ / 96 h / Ambient temperature

8: 94 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

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

10: 100 percent / dl-CSA / methanol; CH₂Cl₂ / 12 h / Ambient temperature

11: 93 percent / imidazole / CH₂Cl₂ / 0.75 h / Ambient temperature

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

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

14: 95 percent / DIBAH / CH₂Cl₂; hexane / 0.5 h / -78 °C

15: 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

16: Et₃N / CH₂Cl₂ / 1.5 h / Ambient temperature

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

18: 96 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

19: 88 percent / DMAP, Et₃N / CH₂Cl₂ / 4 h / Ambient temperature

20: 100 percent / PPTS / CH₂Cl₂ / 2 h / Ambient temperature

21: 89 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

22: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / 0 °C

23: 96 percent / dimethylsulfoxide / 5 h / 80 °C

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

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

26: 100 percent / imidazole / CH₂Cl₂ / 1.5 h / Ambient temperature

27: 95 percent / DDQ, phosphate buffer / CH₂Cl₂ / 1 h / Ambient temperature

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

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

30: 97 percent / diisopropylethylamine, DMAP / CH₂Cl₂ / 33 h / 40 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; 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; 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; zinc(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile;
DOI:10.1248/cpb.45.1265