(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

Base Information

Chemical Name:(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
CAS No.:182411-65-0
Molecular Formula:C₄₁H₈₀O₈Si₄
Molecular Weight:813.423
Hs Code.:

(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

Synonyms:(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

Suppliers and Price of (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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (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

There total 32 articles about (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 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: 68.0%

: 182411-64-9
(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

: 182411-65-0
(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

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1016/0040-4020(96)00700-4

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

: 182411-65-0
(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

Guidance literature:: Multi-step reaction with 29 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

25: OsO₄, N-methylmorpholine N-oxide / acetone; acetonitrile; H₂O; 2-methyl-propan-2-ol / 50 h / Ambient temperature

26: aq. NaIO₄ / tetrahydrofuran / 4 h / Ambient temperature

27: NaBH₄ / methanol / Ambient temperature

28: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

29: 68 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 2 h / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 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; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; 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

: 182411-65-0
(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

Guidance literature:: Multi-step reaction with 21 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

17: OsO₄, N-methylmorpholine N-oxide / acetone; acetonitrile; H₂O; 2-methyl-propan-2-ol / 50 h / Ambient temperature

18: aq. NaIO₄ / tetrahydrofuran / 4 h / Ambient temperature

19: NaBH₄ / methanol / Ambient temperature

20: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

21: 68 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 2 h / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 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; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1016/0040-4020(96)00700-4