methyl 2-((1R,3S,4aS,9aR)-6-amino-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl)acetate

Base Information

Chemical Name:methyl 2-((1R,3S,4aS,9aR)-6-amino-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl)acetate
CAS No.:1438404-31-9
Molecular Formula:C₃₁H₃₇NO₅Si
Molecular Weight:531.724
Hs Code.:

Synonyms:methyl 2-((1R,3S,4aS,9aR)-6-amino-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl)acetate

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Chemical Property of methyl 2-((1R,3S,4aS,9aR)-6-amino-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl)acetate

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Technology Process of methyl 2-((1R,3S,4aS,9aR)-6-amino-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl)acetate

There total 3 articles about methyl 2-((1R,3S,4aS,9aR)-6-amino-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl)acetate 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: 61.0%

: 1438404-27-3
methyl 2-((2R,5R,6R)-5-(4-amino-2-bromophenoxy)-6-(((tertbutyldiphenylsilyl)oxy)methyl)-5,6-dihydro-2H-pyran-2-yl)acetate

: 1438404-31-9
methyl 2-((1R,3S,4aS,9aR)-6-amino-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl)acetate

Guidance literature:: methyl 2-((2R,5R,6R)-5-(4-amino-2-bromophenoxy)-6-(((tertbutyldiphenylsilyl)oxy)methyl)-5,6-dihydro-2H-pyran-2-yl)acetate; With 2,2'-azobis(isobutyronitrile); tributyltin chloride; In isopropyl alcohol; at 85 ℃; for 0.25h; Inert atmosphere;

With 2,2'-azobis(isobutyronitrile); sodium cyanoborohydride; In isopropyl alcohol; benzene; for 4h;
DOI:10.1021/jo4000916

Reference yield:

: 1271303-22-0
C₂₅H₃₂O₅Si

: 1438404-31-9
methyl 2-((1R,3S,4aS,9aR)-6-amino-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl)acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 4.17 h / 0 - 20 °C

2.1: zinc / tetrahydrofuran; acetic acid / 4 h / 20 °C

3.1: 2,2'-azobis(isobutyronitrile); tributyltin chloride / isopropyl alcohol / 0.25 h / 85 °C / Inert atmosphere

3.2: 4 h

With 2,2'-azobis(isobutyronitrile); tributyltin chloride; sodium hydride; zinc; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jo4000916

Reference yield:

: 1438404-21-7
methyl 2-((2R,5R,6R)-5-(2-bromo-4-nitrophenoxy)-6-(((tertbutyldiphenylsilyl)oxy)methyl)-5,6-dihydro-2H-pyran-2-yl)acetate

: 1438404-31-9
methyl 2-((1R,3S,4aS,9aR)-6-amino-1-(((tert-butyldiphenylsilyl)oxy)methyl)-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]benzofuran-3-yl)acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: zinc / tetrahydrofuran; acetic acid / 4 h / 20 °C

2.1: 2,2'-azobis(isobutyronitrile); tributyltin chloride / isopropyl alcohol / 0.25 h / 85 °C / Inert atmosphere

2.2: 4 h

With 2,2'-azobis(isobutyronitrile); tributyltin chloride; zinc; In tetrahydrofuran; acetic acid; isopropyl alcohol;
DOI:10.1021/jo4000916