(2R,3S,4S)-1-O-benzoyl-3-O-tert-butyldiphenylsilyl-4-benzyloxymethyl-5-hexene-1,2-diol

Base Information

Chemical Name:(2R,3S,4S)-1-O-benzoyl-3-O-tert-butyldiphenylsilyl-4-benzyloxymethyl-5-hexene-1,2-diol
CAS No.:245323-07-3
Molecular Formula:C₃₇H₄₂O₅Si
Molecular Weight:594.823
Hs Code.:

Synonyms:(2R,3S,4S)-1-O-benzoyl-3-O-tert-butyldiphenylsilyl-4-benzyloxymethyl-5-hexene-1,2-diol

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Chemical Property of (2R,3S,4S)-1-O-benzoyl-3-O-tert-butyldiphenylsilyl-4-benzyloxymethyl-5-hexene-1,2-diol

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Technology Process of (2R,3S,4S)-1-O-benzoyl-3-O-tert-butyldiphenylsilyl-4-benzyloxymethyl-5-hexene-1,2-diol

There total 6 articles about (2R,3S,4S)-1-O-benzoyl-3-O-tert-butyldiphenylsilyl-4-benzyloxymethyl-5-hexene-1,2-diol 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: 82.0%

: 613-90-1
benzoyl cyanide

: 245323-06-2
(2R,3S,4S)-3-[(tert-butyldiphenylsilyl)oxy]-4-benzyloxymethyl-5-hexene-1,2-diol

: 245323-07-3
(2R,3S,4S)-1-O-benzoyl-3-O-tert-butyldiphenylsilyl-4-benzyloxymethyl-5-hexene-1,2-diol

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo982130k

Reference yield:

: 81028-03-7
(Z)-4-benzyloxy-but-2-en-1-ol

: 245323-07-3
(2R,3S,4S)-1-O-benzoyl-3-O-tert-butyldiphenylsilyl-4-benzyloxymethyl-5-hexene-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1: 83 percent / PPh₃; Br₂; pyridine / benzene; CCl₄ / 2 h

2: 37 percent / Zn; aq. NH₄Cl / tetrahydrofuran / 1.5 h

3: NaH / tetrahydrofuran / 0.5 h / 50 °C

4: 2.84 g / aq. TFA / CH₂Cl₂ / 6 h / 15 °C

5: 82 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With pyridine; bromine; sodium hydride; ammonium chloride; triethylamine; triphenylphosphine; trifluoroacetic acid; zinc; In tetrahydrofuran; tetrachloromethane; dichloromethane; benzene; 1: Substitution / 2: Addition / 3: Substitution / 4: Hydrolysis / 5: Acylation;
DOI:10.1021/jo982130k

Reference yield:

: 100-39-0
benzyl bromide

: 245323-07-3
(2R,3S,4S)-1-O-benzoyl-3-O-tert-butyldiphenylsilyl-4-benzyloxymethyl-5-hexene-1,2-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 78 percent / NaH / tetrahydrofuran / 3.5 h / 50 °C

2: 83 percent / PPh₃; Br₂; pyridine / benzene; CCl₄ / 2 h

3: 37 percent / Zn; aq. NH₄Cl / tetrahydrofuran / 1.5 h

4: NaH / tetrahydrofuran / 0.5 h / 50 °C

5: 2.84 g / aq. TFA / CH₂Cl₂ / 6 h / 15 °C

6: 82 percent / Et₃N / CH₂Cl₂ / 1 h / 0 °C

With pyridine; bromine; sodium hydride; ammonium chloride; triethylamine; triphenylphosphine; trifluoroacetic acid; zinc; In tetrahydrofuran; tetrachloromethane; dichloromethane; benzene; 1: Alkylation / 2: Substitution / 3: Addition / 4: Substitution / 5: Hydrolysis / 6: Acylation;
DOI:10.1021/jo982130k