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

Base Information

Chemical Name:(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-8a(4aH)-ol
CAS No.:1453217-95-2
Molecular Formula:C₃₄H₅₂O₆Si₂
Molecular Weight:612.954
Hs Code.:

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

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

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

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

There total 15 articles about (3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-8a(4aH)-ol 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: 87.0%

: 1453217-97-4
C₃₈H₅₄N₂O₇SSi₂

: 1453217-95-2
(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-8a(4aH)-ol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 110 ℃; for 0.25h;
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

: 1453217-95-2
(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-8a(4aH)-ol

Guidance literature:: Multi-step reaction with 7 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

5: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 7 h / 0 - 23 °C / Inert atmosphere

6: dmap / dichloromethane / 19 h / 40 °C / Inert atmosphere

7: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.25 h / 110 °C

With dmap; 2,2'-azobis(isobutyronitrile); oxygen; tri-n-butyl-tin hydride; copper diacetate; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; palladium dichloride; tetramethylammonium triacetoxyborohydride; In dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; toluene; acetonitrile; 2: |Wacker Oxidation / 4: |Aldol Condensation / 7: |Barton-McCombie Deoxygenation;
DOI:10.1021/jo401170y

Reference yield:

: 1453217-91-8
1,2-O-isopropylidene-3-keto-4-C-(tert-butyldiphenylsilyl)oxymethyl-5-O-(tert-butyldimethylsilyl)-6-deoxy-6-C-vinyl-β-Lmannofuranose

: 1453217-95-2
(3aR,4aS,5S,8aR,8bR)-5-((tert-butyldimethylsilyl)oxy)-4a-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-b]benzofuran-8a(4aH)-ol

Guidance literature:: Multi-step reaction with 5 steps

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

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

3: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 7 h / 0 - 23 °C / Inert atmosphere

4: dmap / dichloromethane / 19 h / 40 °C / Inert atmosphere

5: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.25 h / 110 °C

With dmap; 2,2'-azobis(isobutyronitrile); oxygen; tri-n-butyl-tin hydride; copper diacetate; acetic acid; L-proline; palladium dichloride; tetramethylammonium triacetoxyborohydride; In dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; toluene; acetonitrile; 2: |Aldol Condensation / 5: |Barton-McCombie Deoxygenation;
DOI:10.1021/jo401170y