(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

Base Information

Chemical Name:(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal
CAS No.:885322-69-0
Molecular Formula:C₂₇H₄₂O₃Si₂
Molecular Weight:470.8
Hs Code.:

Synonyms:(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

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Chemical Property of (3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

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Technology Process of (3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

There total 6 articles about (3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal 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: 99.0%

: 885322-68-9
(3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene

: 885322-69-0
(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

Guidance literature:: (3R)-1-[(tert-butyldimethylsilyl)oxy]-3-[(tert-butyldiphenylsilyl)oxy]hex-5-ene; With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; tert-butyl alcohol; at 20 ℃; for 33h;

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 2h;
DOI:10.1021/acs.jnatprod.8b00732

Reference yield:

: 89922-82-7
3-(tert-butyldimethylsilanyloxy)propionaldehyde

: 885322-69-0
(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

Guidance literature:: Multi-step reaction with 3 steps

1.1: (+)-Ipc₂BOMe / diethyl ether / 0 - 20 °C

1.2: diethyl ether / 4 h / -100 °C

1.3: NaOH; H₂O₂ / diethyl ether; H₂O / 20 °C

2.1: 96 percent / imidazole / dimethylformamide / 20 °C

3.1: N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O / 10 h / 20 °C

3.2: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

With 1H-imidazole; osmium(VIII) oxide; 4-methylmorpholine N-oxide; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; 1.2: Brown asymmetric alkylation;
DOI:10.1021/jo060028e

Reference yield:

: 127793-65-1
(3R)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-ol

: 885322-69-0
(3S)-3-[(tert-butyldiphenylsilyl)oxy]-5-[(tert-butyldimethylsilyl)oxy]hexanal

Guidance literature:: Multi-step reaction with 2 steps

1.1: 96 percent / imidazole / dimethylformamide / 20 °C

2.1: N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O / 10 h / 20 °C

2.2: 84 percent / NaIO₄ / tetrahydrofuran; H₂O / 2 h / 20 °C

With 1H-imidazole; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide;
DOI:10.1021/jo060028e