(2S,3R)4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butyraldehyde

Base Information

Chemical Name:(2S,3R)4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butyraldehyde
CAS No.:871345-69-6
Molecular Formula:C₃₆H₄₂O₆Si
Molecular Weight:598.811
Hs Code.:

Synonyms:(2S,3R)4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butyraldehyde

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Chemical Property of (2S,3R)4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butyraldehyde

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Technology Process of (2S,3R)4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butyraldehyde

There total 4 articles about (2S,3R)4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butyraldehyde 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: 91.0%

: 871345-91-4
(1R,1R)-4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butan-1-ol

: 871345-69-6
(2S,3R)4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butyraldehyde

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 2h;
DOI:10.1021/ol052322j

Reference yield:

: 2746-25-0
p-Methoxybenzyl bromide

: 871345-69-6
(2S,3R)4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butyraldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 50 percent / NaH; 18-crown-6 / tetrabutylammonium iodide / tetrahydrofuran / 0 - 20 °C

2: 89 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

3: 82 percent / NaH / tetrahydrofuran / 2 h / 20 °C

4: 91 percent / oxalyl chloride; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

With lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; sodium hydride; dimethyl sulfoxide; triethylamine; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; 4: Swern oxidation;
DOI:10.1021/ol052322j

Reference yield:

: 871345-83-4
(2R,3R)-2,3-Bis-(4-methoxy-benzyloxy)-butane-1,4-diol

: 871345-69-6
(2S,3R)4-[(tert-butyl-diphenylsilyl)-oxy]-2,3-bis-(4-methoxy-benzyloxy)-butyraldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / NaH / tetrahydrofuran / 2 h / 20 °C

2: 91 percent / oxalyl chloride; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / 2 h / -78 - 0 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2: Swern oxidation;
DOI:10.1021/ol052322j