(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one

Base Information

Chemical Name:(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one
CAS No.:1453217-93-0
Molecular Formula:C₃₄H₅₀O₇Si₂
Molecular Weight:626.938
Hs Code.:

(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one

Synonyms:(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one

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Chemical Property of (3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one

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Technology Process of (3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one

There total 11 articles about (3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-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: 82.0%

: 1453217-94-1
C₃₄H₅₀O₇Si₂

: 1453217-93-0
(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one

Guidance literature:: With L-proline; In dimethyl sulfoxide; at 55 ℃; for 54h; Inert atmosphere;
DOI:10.1021/jo401170y

Reference yield:

: 1453217-90-7
1,2-O-isopropylidene-3-O-(2-naphthylmethyl)-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-L-mannofuranose

: 1453217-93-0
(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one

Guidance literature:: Multi-step reaction with 4 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 6 h / 23 °C

2: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 18 h / 23 °C / Inert atmosphere

3: oxygen; copper diacetate; palladium dichloride / water; N,N-dimethyl acetamide / 24 h / 40 °C

4: L-proline / dimethyl sulfoxide / 54 h / 55 °C / Inert atmosphere

With oxygen; copper diacetate; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; palladium dichloride; In dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; 2: |Wacker Oxidation / 4: |Aldol Condensation;
DOI:10.1021/jo401170y

Reference yield:

: 956485-08-8
((3aR,5R,6S,6aR)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

: 1453217-93-0
(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-8a-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-7(4aH)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridinium chlorochromate / dichloromethane / 13 h / 40 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -41 °C / Inert atmosphere

2.2: 2 h / -41 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 3 h / 0 - 23 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 6 h / 23 °C

5.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 18 h / 23 °C / Inert atmosphere

6.1: oxygen; copper diacetate; palladium dichloride / water; N,N-dimethyl acetamide / 24 h / 40 °C

7.1: L-proline / dimethyl sulfoxide / 54 h / 55 °C / Inert atmosphere

With pyridine; boron trifluoride diethyl etherate; oxygen; copper diacetate; sodium hydrogencarbonate; Dess-Martin periodane; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; palladium dichloride; In dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; 2.1: |Sakurai Allylation / 5.1: |Wacker Oxidation / 7.1: |Aldol Condensation;
DOI:10.1021/jo401170y