(3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol

Base Information

Chemical Name:(3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol
CAS No.:716320-22-8
Molecular Formula:C₄₀H₄₈O₆Si
Molecular Weight:652.903
Hs Code.:

Synonyms:(3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol

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Chemical Property of (3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol

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Technology Process of (3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol

There total 9 articles about (3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-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: 90.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 716320-21-7
(3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-hydroxymethyl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol

: 716320-22-8
(3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1002/ejoc.200300339

Reference yield:

: 100-39-0
benzyl bromide

: 716320-22-8
(3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / NaH; Bu₄NI / tetrahydrofuran / 3 h

2: 85 percent / PPTS / methanol / 24 h

3: 90 percent / imidazole / dimethylformamide / 12 h / 20 °C

With 1H-imidazole; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300339

Reference yield:

: 498555-13-8
(4R,5R)-4-[(4R,5R)-5-(1-Hydroxy-prop-2-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,2-dimethyl-[1,3]dioxan-5-ol

: 716320-22-8
(3aS,4R,5S,6S,7S,7aR)-6,7-Bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 57 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 76 percent / pyridine / acetonitrile / 1 h / 85 °C

3: 23 percent / Bu₃SnH; AIBN / toluene / 12 h / 85 °C

4: 70 percent / K₂CO₃ / methanol

5: O₃ / methanol; CH₂Cl₂ / -78 °C

6: 205 mg / NaBH₄; CeCl₃*H₂O / methanol / 0 - 20 °C

7: 72 percent / NaH; Bu₄NI / tetrahydrofuran / 3 h

8: 85 percent / PPTS / methanol / 24 h

9: 90 percent / imidazole / dimethylformamide / 12 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/ejoc.200300339