((2S,3S,4R,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Base Information

Chemical Name:((2S,3S,4R,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
CAS No.:878675-45-7
Molecular Formula:C₃₆H₆₅IO₅Si
Molecular Weight:732.899
Hs Code.:

Synonyms:((2S,3S,4R,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Chemical Property of ((2S,3S,4R,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Technology Process of ((2S,3S,4R,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

There total 7 articles about ((2S,3S,4R,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-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%

: 878675-44-6
(2S,3S,4S,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-ol

: 69739-34-0
t-butyldimethylsiyl triflate

: 878675-45-7
((2S,3S,4R,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 2.5h;
DOI:10.1016/j.tetlet.2005.12.029

Reference yield:

: 878675-43-5
(2R,3R,4S,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-ol

: 878675-45-7
((2S,3S,4R,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 2 steps

1: 74 percent / I₂; PPh₃; imidazole / toluene / 0.5 h / Heating

2: 100 percent / pyridine / CH₂Cl₂ / 2.5 h / 20 °C

With pyridine; 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; toluene; 1: Garreg's iodination;
DOI:10.1016/j.tetlet.2005.12.029

Reference yield:

: (2R,4aR,6S,7R,8S,8aS)-7-Hexadecyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

: 878675-45-7
((2S,3S,4R,5R,6S)-4-Benzyloxy-5-hexadecyloxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1: 72 percent / NaH / dimethylformamide; tetrahydrofuran / 3 h / 20 °C

2: 100 percent / CSA / methanol / 1 h / Heating

3: 74 percent / I₂; PPh₃; imidazole / toluene / 0.5 h / Heating

4: 100 percent / pyridine / CH₂Cl₂ / 2.5 h / 20 °C

With pyridine; 1H-imidazole; camphor-10-sulfonic acid; iodine; sodium hydride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Garreg's iodination;
DOI:10.1016/j.tetlet.2005.12.029