(3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

Base Information

Chemical Name:(3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol
CAS No.:303963-93-1
Molecular Formula:C₂₅H₃₂O₄Si
Molecular Weight:424.612
Hs Code.:

Synonyms:(3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

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

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Chemical Property of (3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

Chemical Property:

Purity/Quality:: 99% ^*data from raw suppliers

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Technology Process of (3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

There total 21 articles about (3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][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: 99.0%

: 303963-92-0
(3aR,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

: 303963-93-1
(3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 - 5 ℃; for 0.5h;
DOI:10.1016/j.tet.2007.06.100

Reference yield: 96.0%

: (R)-1-((4R,5S)-5-(3-(tert-butyldiphenylsilyloxy)prop-1-en-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-en-1-ol

: 303963-93-1
(3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/jo302038d

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 303963-93-1
(3aS,4S,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / triethylamine; DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C

2.2: 86 percent / tetrahydrofuran / 7 h / 0 - 20 °C

3.1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

4.1: 96 percent / tetrahydrofuran / 1 h / -78 °C

5.1: 95 percent / Neolyst dichloride^TM / CH₂Cl₂ / 48 h / 20 °C

6.1: 90 percent / pyridinium dichromate; 4 Angstroem molecular sieves / dimethylformamide / 48 h / 20 °C

7.1: 99 percent / sodium borohydride; cerium(III) chloride heptahydrate / methanol / 0.5 h / 0 - 5 °C

With dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; oxalyl dichloride; 4 A molecular sieve; potassium tert-butylate; dimethyl sulfoxide; triethylamine; Neolyst dichloride^TM; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 2.2: Wittig reaction / 3.1: Swern oxidation / 4.1: Grignard reaction / 7.1: Luche reduction;
DOI:10.1016/j.tet.2007.06.100