3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone

Base Information

Chemical Name:3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone
CAS No.:105676-45-7
Molecular Formula:C₂₅H₃₄O₄S₃Si
Molecular Weight:522.826
Hs Code.:

Synonyms:3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone

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Chemical Property of 3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone

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Technology Process of 3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone

There total 12 articles about 3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone 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: 85.0%

: 39090-54-5
tris(methylthio)methyl lithium

: Lithium; (4S,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-(tris-methylsulfanyl-methyl)-4,5-dihydro-furan-2-olate

: 105676-45-7
3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone

Guidance literature:: With MoO₅*pyridine*HMPA; In tetrahydrofuran; at -78 ℃;

Reference yield:

: 32780-06-6
(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

: 105676-45-7
3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone

Guidance literature:: Multi-step reaction with 5 steps

1: 71.5 percent / triethylamine, 4,4-dimethylaminopyridine / CH₂Cl₂ / 3.5 h / Ambient temperature

2: 1.) lithium hexamethyldisilazide / 1.) THF, hexane, -78 deg C, 25 min; 2.) THF, hexane

3: 30percent H₂O₂ / 0 °C

4: 1.) n-butyl lithium / 1.) THF, hexane, -78 deg C, 20 min; 2.) THF, hexane, -78 deg C, 30 min.

5: 1.) n-butyl lithium, hexamethyldisilazane 3.) oxodiperoxomolybdenum-pyridine-HMPA complex / 1.) THF, 0 deg C, 10 min; 2.) THF, -78 deg C, 20 min; 3.) THF, -60 deg C, 45 min.

With dmap; n-butyllithium; MoO₅*pyridine*HMPA; dihydrogen peroxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hexamethyldisilazane; In dichloromethane;
DOI:10.1016/S0040-4020(01)87683-3

Reference yield:

: 99315-76-1
(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone

: 105676-45-7
3-deoxy-3-tris(methylthio)methyl-5-O-tert-butyldiphenylsilyl-D-arabino-1,4-lactone

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / tetrahydrofuran / -78 °C

2: 85 percent / oxodiperoxymolybdenum(pyridine)hexamethylphosphoramide / tetrahydrofuran / -78 °C

With MoO₅*pyridine*HMPA; In tetrahydrofuran;