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

Base Information

• Chemical Name: (2R,3R,4R,4aR,6S,7S,8S,8aS)-4-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-2,6-divinyl-octahydro-pyrano[3,2-b]pyran
• CAS No.: 182411-62-7
• Molecular Formula: C₃₉H₆₀O₇Si₂
• Molecular Weight: 697.072

Synonyms:

Chemical Property of (2R,3R,4R,4aR,6S,7S,8S,8aS)-4-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-2,6-divinyl-octahydro-pyrano[3,2-b]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,4aR,6S,7S,8S,8aS)-4-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-2,6-divinyl-octahydro-pyrano[3,2-b]pyran

There total 27 articles about (2R,3R,4R,4aR,6S,7S,8S,8aS)-4-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-2,6-divinyl-octahydro-pyrano[3,2-b]pyran 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:

(3aS,4R,7R,7aS)-7-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ol → (2R,3R,4R,4aR,6S,7S,8S,8aS)-4-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-2,6-divinyl-octahydro-pyrano[3,2-b]pyran (182411-62-7)

Guidance literature:

Multi-step reaction with 24 steps

1: 67 percent / benzene / 6 h / Heating

2: 69 percent / TfOH / diethyl ether / Ambient temperature

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

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

5: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

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

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

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

9: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

11: 17 percent / (+)-DET, Ti(Oi-Pr)4, t-BuO₂H / CH₂Cl₂ / 216 h / -25 °C

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

13: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

14: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.17 h / Ambient temperature

15: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

16: 91 percent / CSA / CH₂Cl₂ / 14 h / -40 - 20 °C

17: 100 percent / 2,6-lutidine / CH₂Cl₂ / 27 h / Ambient temperature

18: 96 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

19: 98 percent / L-(+)-DET, Ti(Oi-Pr)4, 4A mol. sieves, t-BuO₂H / CH₂Cl₂ / 24 h / -20 °C

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

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

22: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

23: 12.9 mg / CSA / CH₂Cl₂ / 12 h / -40 - 20 °C

24: 2,6-lutidine / CH₂Cl₂ / 15 h / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; 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; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; benzene;

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

Reference yield:

(2E,8E)-(4R,5R,6S,7S)-7-Benzyloxy-5,6,10-trihydroxy-4-(4-methoxy-benzyloxy)-deca-2,8-dienoic acid ethyl ester → (2R,3R,4R,4aR,6S,7S,8S,8aS)-4-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-2,6-divinyl-octahydro-pyrano[3,2-b]pyran (182411-62-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

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

3: 17 percent / (+)-DET, Ti(Oi-Pr)4, t-BuO₂H / CH₂Cl₂ / 216 h / -25 °C

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

5: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

6: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.17 h / Ambient temperature

7: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

8: 91 percent / CSA / CH₂Cl₂ / 14 h / -40 - 20 °C

9: 100 percent / 2,6-lutidine / CH₂Cl₂ / 27 h / Ambient temperature

10: 96 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

11: 98 percent / L-(+)-DET, Ti(Oi-Pr)4, 4A mol. sieves, t-BuO₂H / CH₂Cl₂ / 24 h / -20 °C

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

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

14: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

15: 12.9 mg / CSA / CH₂Cl₂ / 12 h / -40 - 20 °C

16: 2,6-lutidine / CH₂Cl₂ / 15 h / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; diethyl (2R,3R)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

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

Reference yield:

(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 (182411-35-4) → (2R,3R,4R,4aR,6S,7S,8S,8aS)-4-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-2,6-divinyl-octahydro-pyrano[3,2-b]pyran (182411-62-7)

Guidance literature:

Multi-step reaction with 21 steps

1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

2: 100 percent / TBAF / tetrahydrofuran / 0.5 h / Ambient temperature

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

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

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

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

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

8: 17 percent / (+)-DET, Ti(Oi-Pr)4, t-BuO₂H / CH₂Cl₂ / 216 h / -25 °C

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

10: 99 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

11: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 0.17 h / Ambient temperature

12: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

13: 91 percent / CSA / CH₂Cl₂ / 14 h / -40 - 20 °C

14: 100 percent / 2,6-lutidine / CH₂Cl₂ / 27 h / Ambient temperature

15: 96 percent / K₂CO₃ / methanol / 1 h / Ambient temperature

16: 98 percent / L-(+)-DET, Ti(Oi-Pr)4, 4A mol. sieves, t-BuO₂H / CH₂Cl₂ / 24 h / -20 °C

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

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

19: 91 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature

20: 12.9 mg / CSA / CH₂Cl₂ / 12 h / -40 - 20 °C

21: 2,6-lutidine / CH₂Cl₂ / 15 h / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; diethyl (2R,3R)-tartrate; 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; In tetrahydrofuran; methanol; ethanol; dichloromethane;

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

upstream raw materials:

t-butyldimethylsiyl triflate

(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

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,4R,4aR,6S,7S,8S,8aS)-4-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-6-hydroxymethyl-8-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

(2S,3R,4S,4aS,6R,7R,8R,8aR)-8-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-2,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-octahydro-pyrano[3,2-b]pyran-4-ol

(2R,3R,4R,4aR,6S,7S,8S,8aR)-4-Benzyloxy-3,7,8-tris-(tert-butyl-dimethyl-silanyloxy)-2,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-octahydro-pyrano[3,2-b]pyran

(2R,3R,4R,4aR,6S,7S,8S,8aS)-4-Benzyloxy-3,7-bis-(tert-butyl-dimethyl-silanyloxy)-2,6-bis-(tert-butyl-dimethyl-silanyloxymethyl)-8-(4-methoxy-benzyloxy)-octahydro-pyrano[3,2-b]pyran

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