[(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane
CAS No.:1262295-46-4
Molecular Formula:C₂₇H₄₈O₄Si
Molecular Weight:464.761
Hs Code.:

Synonyms:[(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane

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Technology Process of [(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane

There total 10 articles about [(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-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: 88.0%

: 1262295-45-3
(3R,5R,7S)-7-benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-8,8-dimethyl-nonane-3,5-diol

: 77-76-9
2,2-dimethoxy-propane

: 1262295-46-4
[(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1021/jo101782q

Reference yield:

: 1262295-44-2
(5S,7S)-7-benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-8,8-dimethyl-nonan-3-one

: 1262295-46-4
[(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 2 steps

1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 14 h / -40 - 20 °C / Inert atmosphere

2: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere

With pyridinium p-toluenesulfonate; acetic acid; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetonitrile;
DOI:10.1021/jo101782q

Reference yield:

: 100-39-0
benzyl bromide

: 1262295-46-4
[(S)-3-benzyloxy-4-((4R,6R)-6-ethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-butoxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 9 steps

1.1: silver(l) oxide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere

5.1: borane-THF / tetrahydrofuran / -20 - 20 °C / Inert atmosphere

5.2: 1 h / Inert atmosphere

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 - -30 °C / Inert atmosphere

6.2: 0.5 h / -78 °C / Inert atmosphere

7.1: boron trifluoride diethyl etherate / dichloromethane / 1.25 h / -78 °C / Inert atmosphere

8.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 14 h / -40 - 20 °C / Inert atmosphere

9.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere

With pyridine; dmap; n-butyllithium; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; silver(l) oxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; hexanes; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Swern oxidation / 6.2: Swern oxidation / 7.1: Mukaiyama reaction;
DOI:10.1021/jo101782q