(3aR,4aS,5S,8aR,8bR)-5,8a-bis(benzyloxy)-2,2-dimethyl-4a-((naphthalen-2-ylmethoxy)methyl)octahydro[1,3]dioxolo[4,5-b]benzofuran

Base Information

• Chemical Name: (3aR,4aS,5S,8aR,8bR)-5,8a-bis(benzyloxy)-2,2-dimethyl-4a-((naphthalen-2-ylmethoxy)methyl)octahydro[1,3]dioxolo[4,5-b]benzofuran
• CAS No.: 1453218-00-2
• Molecular Formula: C₃₇H₄₀O₆
• Molecular Weight: 580.721

Synonyms:(3aR,4aS,5S,8aR,8bR)-5,8a-bis(benzyloxy)-2,2-dimethyl-4a-((naphthalen-2-ylmethoxy)methyl)octahydro[1,3]dioxolo[4,5-b]benzofuran

Chemical Property of (3aR,4aS,5S,8aR,8bR)-5,8a-bis(benzyloxy)-2,2-dimethyl-4a-((naphthalen-2-ylmethoxy)methyl)octahydro[1,3]dioxolo[4,5-b]benzofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3aR,4aS,5S,8aR,8bR)-5,8a-bis(benzyloxy)-2,2-dimethyl-4a-((naphthalen-2-ylmethoxy)methyl)octahydro[1,3]dioxolo[4,5-b]benzofuran

There total 19 articles about (3aR,4aS,5S,8aR,8bR)-5,8a-bis(benzyloxy)-2,2-dimethyl-4a-((naphthalen-2-ylmethoxy)methyl)octahydro[1,3]dioxolo[4,5-b]benzofuran 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: 91.0%

C23H28O6 (1453218-03-5) + benzyl bromide (100-39-0) → (3aR,4aS,5S,8aR,8bR)-5,8a-bis(benzyloxy)-2,2-dimethyl-4a-((naphthalen-2-ylmethoxy)methyl)octahydro[1,3]dioxolo[4,5-b]benzofuran (1453218-00-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil; at 0 - 23 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo401170y

Reference yield:

((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 (956485-08-8) → (3aR,4aS,5S,8aR,8bR)-5,8a-bis(benzyloxy)-2,2-dimethyl-4a-((naphthalen-2-ylmethoxy)methyl)octahydro[1,3]dioxolo[4,5-b]benzofuran (1453218-00-2)

Guidance literature:

Multi-step reaction with 14 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

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

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

10.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 0.25 h / 110 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

12.1: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; N,N-dimethyl-formamide; tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 23 °C / Inert atmosphere

14.1: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 0 - 23 °C / Inert atmosphere

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; oxygen; tri-n-butyl-tin hydride; copper diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; L-proline; palladium dichloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 2.1: |Sakurai Allylation / 5.1: |Wacker Oxidation / 7.1: |Aldol Condensation / 10.1: |Barton-McCombie Deoxygenation;

DOI:10.1021/jo401170y

Reference yield:

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 (1453217-90-7) → (3aR,4aS,5S,8aR,8bR)-5,8a-bis(benzyloxy)-2,2-dimethyl-4a-((naphthalen-2-ylmethoxy)methyl)octahydro[1,3]dioxolo[4,5-b]benzofuran (1453218-00-2)

Guidance literature:

Multi-step reaction with 11 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

8: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

9: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; N,N-dimethyl-formamide; tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

10: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 23 °C / Inert atmosphere

11: sodium hydride; tetra-(n-butyl)ammonium iodide / mineral oil; N,N-dimethyl-formamide; tetrahydrofuran / 3 h / 0 - 23 °C / Inert atmosphere

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

DOI:10.1021/jo401170y

upstream raw materials:

((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

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

C₃₄H₅₂O₆Si₂

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

Downstream raw materials:

C₃₄H₃₆O₆

C₃₈H₄₀O₈

(2R,3R,3aR,7S,7aS)-3a,7-bis(benzyloxy)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-7a-((naphthalen-2-ylmethoxy)methyl)octahydrobenzofuran-3-yl acetate

C₃₉H₄₀N₂O₇

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