(3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxyoxolan-2-one

Base Information

Chemical Name:(3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxyoxolan-2-one
CAS No.:102717-30-6
Molecular Formula:C₂₁H₂₆O₄Si
Molecular Weight:370.521
Hs Code.:
DSSTox Substance ID:DTXSID501130192
Nikkaji Number:J1.857.067J

Synonyms:DTXSID501130192;102717-30-6;D-erythro-Pentonic acid, 3-deoxy-5-O-[(1,1-dimethylethyl)diphenylsilyl]-, gamma-lactone

Suppliers and Price of (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxyoxolan-2-one

Supply Marketing:

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

Manufacturers and distributors:

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Total 0 raw suppliers

Chemical Property of (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxyoxolan-2-one

Chemical Property:

Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:370.16003584
Heavy Atom Count:26
Complexity:457

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OCC3CC(C(=O)O3)O
Isomeric SMILES:CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OC[C@@H]3C[C@H](C(=O)O3)O

Technology Process of (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxyoxolan-2-one

There total 5 articles about (3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxyoxolan-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: 73.0%

: 128075-94-5
(R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one

: 1200402-20-5
C₂₁H₂₆O₄Si

: 102717-30-6
(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-dihydro-furan-2-one

Guidance literature:: (R)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}dihydrofuran-2(3H)-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

With MoO₅*pyridine*HMPA; In tetrahydrofuran; at -78 - -30 ℃; for 4h; optical yield given as %de; diastereoselective reaction;
DOI:10.1002/anie.200904603

Reference yield:

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

: 102717-30-6
(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / imidazole / CH₂Cl₂

2: Li(HMDS)2; MeOPH Jacobsen's catalyst / tetrahydrofuran / -78 °C

With 1H-imidazole; MeOPH Jacobsen's catalyst; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(02)02532-7

Reference yield:

: 102717-29-3
(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

: 102717-30-6
(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-dihydro-furan-2-one

Guidance literature:: With MeOPH Jacobsen's catalyst; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(02)02532-7