(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal

Base Information

Chemical Name:(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal
CAS No.:163275-31-8
Molecular Formula:C₂₈H₄₂O₅Si
Molecular Weight:486.724
Hs Code.:

Synonyms:(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal

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Chemical Property of (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal

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Technology Process of (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal

There total 13 articles about (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal 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: 97.0%

: 201284-14-2
(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanol

: 163275-31-8
(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
DOI:10.1246/cl.1995.179

Reference yield: 87.0%

: (3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal dimethyl acetal

: 163275-31-8
(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal

Guidance literature:: With water; acetic acid; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

Reference yield:

: 60856-63-5
(2R)-(-)-3,3-dimethylbutane-1,2,4-triol

: 163275-31-8
(3R,4S)-4-Benzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-2,2-dimethylpentanal

Guidance literature:: Multi-step reaction with 8 steps

1.1: camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

1.2: 92 percent / Et₃N / CH₂Cl₂

2.1: 21.2 g / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

3.1: 86 percent / n-BuLi / hexane; tetrahydrofuran / -15 - 20 °C

4.1: OsO₄; N-methylmorpholine-N-oxide / H₂O; acetone; 2-methyl-propan-2-ol / 72 h / 2 °C

5.1: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

6.1: 96 percent / NaH / tetrahydrofuran; dimethylformamide / 18 h / 0 - 20 °C

7.1: 85 percent / BH₃*Me₂S / toluene / 0.5 h / Heating

8.1: 67 percent / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 2.1: Swern's oxidation / 3.1: Wittig reaction / 8.1: Swern's oxidation;
DOI:10.1246/bcsj.74.113