(2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)hexanal

Base Information

Chemical Name:(2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)hexanal
CAS No.:136904-88-6
Molecular Formula:C₃₁H₄₇NO₆Si
Molecular Weight:557.803
Hs Code.:

Synonyms:(2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)hexanal

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)hexanal

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Technology Process of (2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)hexanal

There total 7 articles about (2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)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:

: 108818-01-5
(2S,3R,4S,5S)-6-<(tert-butyldimethylsilyl)oxy>-2,3-epoxy-4,5-(isopropylidenedioxy)hexan-1-ol

: 136904-88-6
(2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)hexanal

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) triethylaluminum / 1.) CH₂Cl₂, hexane, 30 min, 2.) CH₂Cl₂, r.t., 14 h

2: 88 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 85 percent / N,N-diisopropylethylamine / CHCl₃ / 1 h / Heating

4: 91 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.

With lithium aluminium tetrahydride; oxalyl dichloride; triethylaluminum; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; chloroform;
DOI:10.1021/jo00053a015

Reference yield:

: 136904-87-5
(2R,3R,4S,5S)-1-Acetoxy-6-<(tert-butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)hexane

: 136904-88-6
(2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)hexanal

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.

With lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In diethyl ether;
DOI:10.1021/jo00053a015

Reference yield:

: 136904-86-4
(2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)hexane-1,3-diol

: 136904-88-6
(2R,3R,4S,5S)-6-<(tert-Butyldimethylsilyl)oxy>-2-(dibenzylamino)-4,5-(isopropylidenedioxy)-3-(methoxymethoxy)hexanal

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 85 percent / N,N-diisopropylethylamine / CHCl₃ / 1 h / Heating

3: 91 percent / LiAlH₄ / diethyl ether / 2 h / Ambient temperature

4: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -80 deg C, 2 h, 2.) -80 deg C to r.t.

With lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; chloroform;
DOI:10.1021/jo00053a015