N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide

Base Information

Chemical Name:N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide
CAS No.:569359-01-9
Molecular Formula:C₂₀H₂₉NO₈S
Molecular Weight:443.518
Hs Code.:

<i>N</i>-benzyl-<i>C</i>-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-<i>d</i>][1,3]dioxol-6-yl]-methanesulfonamide

Synonyms:N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide

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Chemical Property of N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide

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Technology Process of N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide

There total 3 articles about N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide 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: 73.0%

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

: 3989-45-5
N-benzylmethanesulfonamide

: 569359-01-9
N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide

Guidance literature:: N-benzylmethanesulfonamide; With n-butyllithium; In tetrahydrofuran; at -75 - -30 ℃; for 1h;

With cerium(III) chloride; In tetrahydrofuran; at -75 - -30 ℃; for 1h;

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose; In tetrahydrofuran; at -75 - -30 ℃;
DOI:10.1021/jo034001w

Reference yield:

: 100-46-9
benzylamine

: 569359-01-9
N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / diethyl ether / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -75 - -30 °C

2.2: CeCl₃ / tetrahydrofuran / 1 h / -75 - -30 °C

2.3: 73 percent / tetrahydrofuran / -75 - -30 °C

With n-butyllithium; In tetrahydrofuran; diethyl ether;
DOI:10.1021/jo034001w

Reference yield:

: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

: 569359-01-9
N-benzyl-C-[5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-methanesulfonamide

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / Dess-Martin periodinate / CH₂Cl₂ / 0 - 20 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -75 - -30 °C

2.2: CeCl₃ / tetrahydrofuran / 1 h / -75 - -30 °C

2.3: 73 percent / tetrahydrofuran / -75 - -30 °C

With n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo034001w