3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-ol

Base Information

Chemical Name:3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-ol
CAS No.:213754-96-2
Molecular Formula:C₃₈H₆₀O₆Si
Molecular Weight:640.976
Hs Code.:

Synonyms:3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-ol

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Chemical Property of 3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-ol

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Technology Process of 3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-ol

There total 10 articles about 3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-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: 90.0%

: 213754-94-0
[(2R,4R,4aS,6S,7R,8aS)-2-Allyl-7-benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-octahydro-pyrano[3,2-b]pyran-4-yloxy]-triisopropyl-silane

: 213754-96-2
3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-ol

Guidance literature:: With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(98)01310-0

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 213754-96-2
3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-lutidine / dimethylformamide / 70 °C

2: 88 percent / LiAlH₄ / diethyl ether / 0 °C

3: 1.) (COCl)2, 2.) Et₃N, 3.) NaHMDS / 1.) DMSO/CH₂Cl₂, -78 deg C, 2.) DMSO/CH₂Cl₂, -78 deg C -> RT, 3.) THF, 0 deg C

4: 90 percent / 9-BBN / tetrahydrofuran / Ambient temperature

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(98)01310-0

Reference yield:

: 213754-77-9
(2S,3S,5R,6S)-5-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6-dimethyl-tetrahydro-pyran-2-carbaldehyde

: 213754-96-2
3-[(2R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-4a,6-dimethyl-4-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: tetrahydrofuran / -78 °C

2: OsO₄, NaIO₄ / tetrahydrofuran; H₂O / Ambient temperature

3: CH₂Cl₂ / Heating

4: 100 percent / TBAF / tetrahydrofuran / 0 °C

5: 75 percent / K₂CO₃ / tetrahydrofuran; methanol / 40 °C

6: 2,6-lutidine / dimethylformamide / 70 °C

7: 88 percent / LiAlH₄ / diethyl ether / 0 °C

8: 1.) (COCl)2, 2.) Et₃N, 3.) NaHMDS / 1.) DMSO/CH₂Cl₂, -78 deg C, 2.) DMSO/CH₂Cl₂, -78 deg C -> RT, 3.) THF, 0 deg C

9: 90 percent / 9-BBN / tetrahydrofuran / Ambient temperature

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(98)01310-0