(3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one

Base Information

• Chemical Name: (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one
• CAS No.: 92512-33-9
• Molecular Formula: C₂₁H₂₆O₅Si
• Molecular Weight: 386.52

Synonyms:(3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one

Chemical Property of (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one

Chemical Property:

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Technology Process of (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one

There total 12 articles about (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-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: 89.0%

(5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone (99315-76-1) → (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one (92512-33-9)

Guidance literature:

With potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide; citric acid; In ethanol; water; at 20 ℃; for 18h; Reagent/catalyst; Solvent; diastereoselective reaction;

DOI:10.1002/ejoc.201801780

Reference yield: 85.0%

tert-butylchlorodiphenylsilane (58479-61-1) + D-Ribono-1,4-lactone (5336-08-3) → 3,5-O-bis(O-diphenyl-t-butylsilyl)-D-ribonic acid γ-lactone (92512-34-0) + (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one (92512-33-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 20h; Ambient temperature;

Reference yield: 72.0%

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3) → (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one (92512-33-9)

Guidance literature:

With acetic acid; for 1.5h; Heating;

DOI:10.1016/0008-6215(94)80066-9

upstream raw materials:

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

tert-butylchlorodiphenylsilane

D-Ribono-1,4-lactone

2,3-O-isopropylidene-D-ribonic-γ-lactone

Downstream raw materials:

2,3-di-O-acetyl-5-O-diphenyl-t-butylsilyl-D-ribonic acid γ-lactone

(-)-5-O-(diphenyl-t-butylsilyl)-2,3-O-(thiocarbonyl)-D-ribono-1,4-lactone

(S)-5-((tert-butyldiphenylsilyloxy)methyl)-2-oxo-2,5-dihydrofuran-3-yl trifluoromethanesulfonate

D-Ribono-1,4-lactone

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