(2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime]

Base Information

Chemical Name:(2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime]
CAS No.:301851-34-3
Molecular Formula:C₄₃H₅₃NO₈Si₂
Molecular Weight:768.067
Hs Code.:

(2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime]

Synonyms:(2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime]

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Chemical Property of (2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime]

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Technology Process of (2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime]

There total 11 articles about (2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime] 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: 57.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 218767-20-5
(2R,3S,4R,1'R)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-hydroxymethyl-5-oxotetrahydrofuran-3-carbaldehyde oxime

: 301851-34-3
(2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime]

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1021/jo000665j

Reference yield:

: 14496-24-3
3,4-bis(hydroxymethyl)furan

: 301851-34-3
(2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime]

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine-SO₃

2: 80 percent / diethyl ether / 1.5 h / 0 - 20 °C

3: 59 percent / AD-mix α; K3Fe(CN)6; K2CO3 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 3 h / 0 - 20 °C

4: 69 percent / TsOH / dimethylformamide / 21 h / 20 °C

5: 74 percent / i-Pr₂NEt; rose bengal; O₂ / CH₂Cl₂ / 11 h / -20 °C / Irradiation

6: 66 percent / OsO₄ / pyridine; 2-methyl-propan-2-ol / 24 h / 0 - 20 °C

7: 94 percent / HONH₂*HCl / tetrahydrofuran; methanol; pyridine / 5.5 h / 70 °C

8: PPTS / methanol / 15 h / 65 °C

9: 101.8 mg / PPTS / dimethylformamide / 5.5 h / 20 °C

10: 57 percent / imidazole / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; AD-mix-α; osmium(VIII) oxide; hydroxylamine hydrochloride; oxygen; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; rose bengal; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Oxidation / 2: Grignard reaction / 3: Oxidation / 4: Cyclization / 5: Oxidation / 6: Oxidation / 7: Ring cleavage / 8: Ring cleavage / 9: Cyclization / 10: silylation;
DOI:10.1021/jo000665j

Reference yield:

: 7040-25-7
3,4-diformylfuran

: 301851-34-3
(2R,3S,4R,1'R)-2-(tert-butyldiphenylsilyloxymethyl)-4-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-5-oxotetrahydrofuran-3-[(tert-butyldiphenylsilyloxy)carbaldehyde oxime]

Guidance literature:: Multi-step reaction with 9 steps

1: 80 percent / diethyl ether / 1.5 h / 0 - 20 °C

2: 59 percent / AD-mix α; K3Fe(CN)6; K2CO3 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 3 h / 0 - 20 °C

3: 69 percent / TsOH / dimethylformamide / 21 h / 20 °C

4: 74 percent / i-Pr₂NEt; rose bengal; O₂ / CH₂Cl₂ / 11 h / -20 °C / Irradiation

5: 66 percent / OsO₄ / pyridine; 2-methyl-propan-2-ol / 24 h / 0 - 20 °C

6: 94 percent / HONH₂*HCl / tetrahydrofuran; methanol; pyridine / 5.5 h / 70 °C

7: PPTS / methanol / 15 h / 65 °C

8: 101.8 mg / PPTS / dimethylformamide / 5.5 h / 20 °C

9: 57 percent / imidazole / dimethylformamide / 16 h / 20 °C

With 1H-imidazole; AD-mix-α; osmium(VIII) oxide; hydroxylamine hydrochloride; oxygen; pyridinium p-toluenesulfonate; rose bengal; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Grignard reaction / 2: Oxidation / 3: Cyclization / 4: Oxidation / 5: Oxidation / 6: Ring cleavage / 7: Ring cleavage / 8: Cyclization / 9: silylation;
DOI:10.1021/jo000665j