(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-octahydro-pyrano[3,2-b]pyran

Base Information

Chemical Name:(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-octahydro-pyrano[3,2-b]pyran
CAS No.:189348-20-7
Molecular Formula:C₃₉H₆₄O₆Si₂
Molecular Weight:685.105
Hs Code.:

(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-octahydro-pyrano[3,2-b]pyran

Synonyms:(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-octahydro-pyrano[3,2-b]pyran

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Chemical Property of (2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-octahydro-pyrano[3,2-b]pyran

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Technology Process of (2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-octahydro-pyrano[3,2-b]pyran

There total 15 articles about (2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-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: 98.0%

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 189348-00-3
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

: 189348-20-7
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃;
DOI:10.1021/ja9701523

Reference yield:

: 189347-91-9
benzyl 3-(3-O-benzyl-2-deoxy-α-D-allopyranosyl)propyl ether

: 189348-20-7
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) 2,6-lutidine / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 30 min

2: 90 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min

3: 90 percent / p-TsOH*H₂O / CHCl₃ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

4: 92 percent / NaBH₄ / methanol; CH₂Cl₂ / 2 h / -78 °C

5: 98 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

6: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform;
DOI:10.1021/jo980320p

Reference yield:

: 189347-96-4
Trifluoro-methanesulfonic acid (2R,3S,4S,6R)-4-benzyloxy-6-(3-benzyloxy-propyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

: 189348-20-7
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-2-triethylsilanyloxymethyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min

2: 90 percent / p-TsOH*H₂O / CHCl₃ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

3: 92 percent / NaBH₄ / methanol; CH₂Cl₂ / 2 h / -78 °C

4: 98 percent / Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

5: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform;
DOI:10.1021/jo980320p