(1S,2S,3R,4S,5S)-4-(tert-butyldiphenylsilyloxy)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Base Information

Chemical Name:(1S,2S,3R,4S,5S)-4-(tert-butyldiphenylsilyloxy)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane
CAS No.:228394-02-3
Molecular Formula:C₃₈H₄₄O₄Si
Molecular Weight:592.85
Hs Code.:

Synonyms:(1S,2S,3R,4S,5S)-4-(tert-butyldiphenylsilyloxy)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

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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 (1S,2S,3R,4S,5S)-4-(tert-butyldiphenylsilyloxy)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

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Technology Process of (1S,2S,3R,4S,5S)-4-(tert-butyldiphenylsilyloxy)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

There total 6 articles about (1S,2S,3R,4S,5S)-4-(tert-butyldiphenylsilyloxy)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane 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: 100.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 199122-46-8
(1S,2S,3R,4S,5S)-1,2-di<(benzyloxy)methyl>-3,4-dihydroxybicyclo<3.1.0>hexane

: 228394-02-3
(1S,2S,3R,4S,5S)-4-(tert-butyldiphenylsilyloxy)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: With 1H-imidazole; In dichloromethane; at 10 ℃; for 5h;
DOI:10.1021/jo990010m

Reference yield:

: 199122-31-1
(1S,2R,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxy-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

: 228394-02-3
(1S,2S,3R,4S,5S)-4-(tert-butyldiphenylsilyloxy)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / TPAP, NMO, 4A MS / CH₂Cl₂ / 0.67 h / Ambient temperature

2: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

3: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

4: 88 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Heating

5: 100 percent / aq. HCl / tetrahydrofuran; methanol / 10 h / Heating

6: 100 percent / imidazole / CH₂Cl₂ / 5 h / 10 °C

With 1H-imidazole; hydrogenchloride; sodium perborate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/jo990010m

Reference yield:

: 199122-41-3
(1S,2S,3R,4S,5S)-1-<(benzyloxy)methyl>-2-hydroxymethyl-3,4-(isopropylidenedioxy)bicyclo<3.1.0>hexane

: 228394-02-3
(1S,2S,3R,4S,5S)-4-(tert-butyldiphenylsilyloxy)-1,2-di<(benzyloxy)methyl>-3-hydroxybicyclo<3.1.0>hexane

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / NaH, n-Bu₄NI / tetrahydrofuran / 15 h / Heating

2: 100 percent / aq. HCl / tetrahydrofuran; methanol / 10 h / Heating

3: 100 percent / imidazole / CH₂Cl₂ / 5 h / 10 °C

With 1H-imidazole; hydrogenchloride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo990010m