((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Base Information

Chemical Name:((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
CAS No.:436153-56-9
Molecular Formula:C₂₇H₃₈O₄Si
Molecular Weight:454.682
Hs Code.:

Synonyms:((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Chemical Property of ((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Technology Process of ((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

There total 10 articles about ((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 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%

: 436153-85-4
((2R,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-iodomethyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

: 436153-56-9
((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/ol025814u

Reference yield:

: 100-39-0
benzyl bromide

: 436153-56-9
((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1: KOt-Bu / tetrahydrofuran / 1 h / 20 °C

2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

3: sodium periodate / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 1 h / 20 °C

4: 8.39 g / sodium borohydride / methanol / 0.33 h / 0 °C

5: 81 percent / iodide; triphenylphosphane; imidazole / benzene / 0.5 h / 20 °C

6: 100 percent / KOt-Bu / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; potassium tert-butylate; iodide; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; methanol; water; tert-butyl alcohol; benzene;
DOI:10.1021/ol025814u

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 436153-56-9
((3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1: 81 percent / imidazole / dimethylformamide / 20 °C

2: 99 percent / EtSH; Zn(OTf)2; NaHCO₃ / CH₂Cl₂ / 8.5 h / 20 °C

3: KOt-Bu / tetrahydrofuran / 1 h / 20 °C

4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 5 h / 20 °C

5: sodium periodate / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 1 h / 20 °C

6: 8.39 g / sodium borohydride / methanol / 0.33 h / 0 °C

7: 81 percent / iodide; triphenylphosphane; imidazole / benzene / 0.5 h / 20 °C

8: 100 percent / KOt-Bu / tetrahydrofuran / 2 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; potassium tert-butylate; iodide; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triphenylphosphine; ethanethiol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
DOI:10.1021/ol025814u