[(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane

Base Information

Chemical Name:[(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane
CAS No.:1309930-46-8
Molecular Formula:C₂₀H₃₁IO₂Si
Molecular Weight:458.455
Hs Code.:

Synonyms:[(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane

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Chemical Property of [(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane

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Technology Process of [(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane

There total 7 articles about [(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane 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: 94.0%

: 1309930-44-6
(1R,5R,6S)-5-tert-butyldimethylsilyloxy-2-iodo-6-methylcyclohex-2-enol

: 100-39-0
benzyl bromide

: 1309930-46-8
[(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane

Guidance literature:: (1R,5R,6S)-5-tert-butyldimethylsilyloxy-2-iodo-6-methylcyclohex-2-enol; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 12h; Inert atmosphere;
DOI:10.1039/c0ob01118e

Reference yield:

: 1309930-37-7
(5R,6R)-5-tert-butyldimethylsilyloxy-6-methyl-2-cyclohexenone

: 1309930-46-8
[(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; iodine / dichloromethane / 10.3 h / 20 °C

2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 0.5 h / 0 °C

3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 12 h / 20 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; iodine; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; 2.1: Luche reduction;
DOI:10.1039/c0ob01118e

Reference yield:

: 1309930-42-4
(5R,6R)-5-tert-butyldimethylsilyloxy-2-iodo-6-methyl-2-cyclohexenone

: 1309930-46-8
[(1R,5R,6S)-5-benzyloxy-4-iodo-6-methylcyclohex-3-enyloxy]-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / 0.5 h / 0 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; 1.1: Luche reduction;
DOI:10.1039/c0ob01118e