N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide

Base Information

Chemical Name:N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide
CAS No.:322648-65-7
Molecular Formula:C₄₆H₅₆INO₁₂SSi
Molecular Weight:1002.01
Hs Code.:

N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide

Synonyms:N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide

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Chemical Property of N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide

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Technology Process of N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide

There total 9 articles about N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide 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: 90.0%

: 98-10-2
benzenesulfonamide

: 322648-64-6
(3aS,4R,6R,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-6-((2R,3S,4R)-2-benzyloxymethyl-3-triethylsilanyloxy-3,4-dihydro-2H-pyran-4-yloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

: 322648-65-7
N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide

Guidance literature:: With iodonium(di-γ-collidine) perchlorate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ja0022730

Reference yield:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 322648-65-7
N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 70 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

3: ZnCl₂ / benzene; tetrahydrofuran; diethyl ether / 4 h / 20 °C

4: 82 percent / NaH / dimethylformamide / 1.5 h / 0 °C

5: 90 percent / I(sym-coll)2ClO₄; 4A MS / CH₂Cl₂ / 1 h / 0 °C

With iodonium(di-γ-collidine) perchlorate; sodium hydride; diisobutylaluminium hydride; triethylamine; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja0022730

Reference yield:

: 165524-85-6
6-O-(benzyl)-D-glucal

: 322648-65-7
N-[(2S,3S,4S,5R,6R)-4-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-3-iodo-5-triethylsilanyloxy-tetrahydro-pyran-2-yl]-benzenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / DMAP; pyridine / CH₂Cl₂

2: 96 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: 70 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

4: ZnCl₂ / benzene; tetrahydrofuran; diethyl ether / 4 h / 20 °C

5: 82 percent / NaH / dimethylformamide / 1.5 h / 0 °C

6: 90 percent / I(sym-coll)2ClO₄; 4A MS / CH₂Cl₂ / 1 h / 0 °C

With pyridine; dmap; iodonium(di-γ-collidine) perchlorate; sodium hydride; diisobutylaluminium hydride; triethylamine; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja0022730