(3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one

Base Information

Chemical Name:(3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one
CAS No.:158587-49-6
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

Synonyms:(3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one

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Chemical Property of (3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one

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Technology Process of (3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one

There total 9 articles about (3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one 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%

: 69739-34-0
t-butyldimethylsiyl triflate

: 158587-60-1
(3S,4S)-3-((R)-4-Benzyloxy-1-hydroxy-butyl)-4-methyl-dihydro-furan-2-one

: 158587-49-6
(3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one

Guidance literature:: With 2,3,5-trimethyl-pyridine; In dichloromethane; -78 deg C to r.t.;
DOI:10.1016/S0040-4039(00)78234-7

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 158587-49-6
(3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) freshly distilled di-n-butylboron triflate; 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) CH₂Cl₂, -78 to 0 deg C, 1 h; 3.) CH₂Cl₂, -78 to 0 deg C, 1 h

2: 48percent aq. HF / acetonitrile / 0.33 h / Ambient temperature

3: sat aq. NaHCO₃, K₂CO₃ / acetonitrile; H₂O / 2 h

4: 97 percent / collidine / CH₂Cl₂ / -78 deg C to r.t.

With 2,3,5-trimethyl-pyridine; hydrogen fluoride; sodium hydrogencarbonate; potassium carbonate; triethylamine; In dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4039(00)78234-7

Reference yield:

: 123444-68-8
(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

: 158587-49-6
(3S,4S)-3-[(R)-4-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-butyl]-4-methyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1 M KMnO₄, 0.5 M NaH₂PO₄ / 2-methyl-propan-2-ol / 0.25 h

2: triethylamine / tetrahydrofuran / 0.5 h / 0 deg C to r.t.

3: n-butyllithium / tetrahydrofuran / 2 h / -78 deg C to r.t.

4: 1.) freshly distilled di-n-butylboron triflate; 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h; 2.) CH₂Cl₂, -78 to 0 deg C, 1 h; 3.) CH₂Cl₂, -78 to 0 deg C, 1 h

5: 48percent aq. HF / acetonitrile / 0.33 h / Ambient temperature

6: sat aq. NaHCO₃, K₂CO₃ / acetonitrile; H₂O / 2 h

7: 97 percent / collidine / CH₂Cl₂ / -78 deg C to r.t.

With 2,3,5-trimethyl-pyridine; potassium permanganate; sodium dihydrogenphosphate; n-butyllithium; hydrogen fluoride; sodium hydrogencarbonate; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4039(00)78234-7