((3aS,4R,6S,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((3aS,4R,6S,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-tert-butyl-dimethyl-silane
• CAS No.: 182411-30-9
• Molecular Formula: C₂₅H₄₀O₆Si
• Molecular Weight: 464.674

Synonyms:((3aS,4R,6S,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-tert-butyl-dimethyl-silane

Chemical Property of ((3aS,4R,6S,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of ((3aS,4R,6S,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-tert-butyl-dimethyl-silane

There total 1 articles about ((3aS,4R,6S,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-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%

benzyl bromide (100-39-0) + (3aS,4R,6S,7R,7aR)-6-Allyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (182411-29-6) → ((3aS,4R,6S,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-tert-butyl-dimethyl-silane (182411-30-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 15h; Ambient temperature;

DOI:10.1016/0040-4020(96)00700-4

Reference yield:

((3aS,4R,6S,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-tert-butyl-dimethyl-silane (182411-30-9) → (2R,3S,4R,5S,6S)-2-[(S)-Benzyloxy-((2R,3S)-3-vinyl-oxiranyl)-methyl]-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-6-vinyl-tetrahydro-pyran (182411-59-2)

Guidance literature:

Multi-step reaction with 22 steps

1: 1.) (PPh₃)3RhCl, (i-Pr)2NEt, 2.) HgO, HgCl₂ / 1.) EtOH, reflux, 3 h, 2.) acetone, water, RT, 30 min

2: 67 percent / benzene / 6 h / Heating

3: 69 percent / TfOH / diethyl ether / Ambient temperature

4: 1.) DIBAL, 2.) NaBH₄, CeCl₃ / 1.) dichloromethane, hexane, -78 deg C, 30 min, 2.) MeOH, RT

5: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

6: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

7: (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

8: 1.) t-BuOK / 1.) THF, 0 deg C, 1.5 h, 2.) THF, -78 deg C, 30 min

9: PTS*H₂O / ethanol / 25 h / Ambient temperature

10: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

11: 1.) DIBAL_. 2.) NaBH₄, CeCl₃*7H₂O / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) MeOH, RT

12: 17 percent / (+)-DET, Ti(Oi-Pr)4, t-BuO₂H / CH₂Cl₂ / 216 h / -25 °C

13: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 1.5 h, 2.) THF, 0 deg C, 30 min

14: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

15: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.17 h / Ambient temperature

16: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

17: 91 percent / CSA / CH₂Cl₂ / 14 h / -40 - 20 °C

18: 100 percent / 2,6-lutidine / CH₂Cl₂ / 27 h / Ambient temperature

19: 96 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

20: 98 percent / L-(+)-DET, Ti(Oi-Pr)4, 4A mol. sieves, t-BuO₂H / CH₂Cl₂ / 24 h / -20 °C

21: (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

22: 1.) NaHMDS / 1.) THF, 0 deg C, 1 h, 2.) THF, 0 deg C, 20 min

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; Wilkinson's catalyst; cerium(III) chloride; oxalyl dichloride; diethyl (2R,3R)-tartrate; trifluorormethanesulfonic acid; 4 A molecular sieve; PTS*H₂O; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1016/0040-4020(96)00700-4

Reference yield:

((3aS,4R,6S,7R,7aS)-6-Allyloxy-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-tert-butyl-dimethyl-silane (182411-30-9) → (2R,3S)-3-{(S)-Benzyloxy-[(2R,3S,4R,5S,6S)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-6-vinyl-tetrahydro-pyran-2-yl]-methyl}-oxirane-2-carbaldehyde

Guidance literature:

Multi-step reaction with 21 steps

1: 1.) (PPh₃)3RhCl, (i-Pr)2NEt, 2.) HgO, HgCl₂ / 1.) EtOH, reflux, 3 h, 2.) acetone, water, RT, 30 min

2: 67 percent / benzene / 6 h / Heating

3: 69 percent / TfOH / diethyl ether / Ambient temperature

4: 1.) DIBAL, 2.) NaBH₄, CeCl₃ / 1.) dichloromethane, hexane, -78 deg C, 30 min, 2.) MeOH, RT

5: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

6: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

7: (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

8: 1.) t-BuOK / 1.) THF, 0 deg C, 1.5 h, 2.) THF, -78 deg C, 30 min

9: PTS*H₂O / ethanol / 25 h / Ambient temperature

10: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

11: 1.) DIBAL_. 2.) NaBH₄, CeCl₃*7H₂O / 1.) CH₂Cl₂, hexane, -78 deg C, 30 min, 2.) MeOH, RT

12: 17 percent / (+)-DET, Ti(Oi-Pr)4, t-BuO₂H / CH₂Cl₂ / 216 h / -25 °C

13: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 1.5 h, 2.) THF, 0 deg C, 30 min

14: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

15: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.17 h / Ambient temperature

16: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

17: 91 percent / CSA / CH₂Cl₂ / 14 h / -40 - 20 °C

18: 100 percent / 2,6-lutidine / CH₂Cl₂ / 27 h / Ambient temperature

19: 96 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

20: 98 percent / L-(+)-DET, Ti(Oi-Pr)4, 4A mol. sieves, t-BuO₂H / CH₂Cl₂ / 24 h / -20 °C

21: (COCl)2, DMSO / CH₂Cl₂ / 1 h / -78 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; Wilkinson's catalyst; cerium(III) chloride; oxalyl dichloride; diethyl (2R,3R)-tartrate; trifluorormethanesulfonic acid; 4 A molecular sieve; PTS*H₂O; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1016/0040-4020(96)00700-4

upstream raw materials:

benzyl bromide

(3aS,4R,6S,7R,7aR)-6-Allyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Downstream raw materials:

(2R,3R,4S,4aR,6S,7S,8R,8aS)-4-Benzyloxy-8-(4-methoxy-benzyloxy)-2,6-divinyl-octahydro-pyrano[3,2-b]pyran-3,7-diol

(2S,3S,4R,5S,6S)-2-[(R)-Benzyloxy-((2R,3S)-3-vinyl-oxiranyl)-methyl]-4-(4-methoxy-benzyloxy)-6-vinyl-tetrahydro-pyran-3,5-diol

(E)-(S)-4-Benzyloxy-4-{(4R,5S)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-but-2-en-1-ol

(2E,4S,5R,6S,7R)-4-O-benzyl-5,6-O-isopropylidene-7-O-(p-methoxybenzyl)-1-O-tetrahydropyranyloct-2-ene-1,4,5,6,7,8-hexaol

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