Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4S,5S,6S)-6-benzenesulfonylamino-2-benzyloxymethyl-5-iodo-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

Base Information

Chemical Name:Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4S,5S,6S)-6-benzenesulfonylamino-2-benzyloxymethyl-5-iodo-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
CAS No.:202657-38-3
Molecular Formula:C₄₁H₅₂INO₁₃SSi
Molecular Weight:953.919
Hs Code.:

Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4S,5S,6S)-6-benzenesulfonylamino-2-benzyloxymethyl-5-iodo-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

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

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

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

There total 10 articles about Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4S,5S,6S)-6-benzenesulfonylamino-2-benzyloxymethyl-5-iodo-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 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: 81.0%

: 98-10-2
benzenesulfonamide

: 202657-34-9
Acetic acid (3aS,4R,6S,7R,7aS)-4-benzyloxymethyl-6-((2R,3R,4R)-2-benzyloxymethyl-4-triethylsilanyloxy-3,4-dihydro-2H-pyran-3-yloxy)-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

: 202657-38-3
Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4S,5S,6S)-6-benzenesulfonylamino-2-benzyloxymethyl-5-iodo-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

Guidance literature:: With iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1021/ja9725864

Reference yield:

: 100-39-0
benzyl bromide

: 202657-38-3
Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4S,5S,6S)-6-benzenesulfonylamino-2-benzyloxymethyl-5-iodo-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / NaH / dimethylformamide / 1 h

2: 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 1 h / 0 °C

3: ZnCl₂ / tetrahydrofuran; diethyl ether / 24 h / Ambient temperature

4: 100 percent / Et₃N, DMAP / CH₂Cl₂

5: 81 percent / 4A molecular sieves, I(sym-coll)2ClO₄ / CH₂Cl₂ / 1 h / Ambient temperature

With dmap; iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; 3,3-dimethyldioxirane; sodium hydride; triethylamine; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja9725864

Reference yield:

: 994-30-9
triethylsilyl chloride

: 202657-38-3
Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4S,5S,6S)-6-benzenesulfonylamino-2-benzyloxymethyl-5-iodo-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / imidazole, DMAP / CH₂Cl₂ / 4 h / -40 °C

2: ZnCl₂ / tetrahydrofuran; diethyl ether / 24 h / Ambient temperature

3: 100 percent / Et₃N, DMAP / CH₂Cl₂

4: 81 percent / 4A molecular sieves, I(sym-coll)2ClO₄ / CH₂Cl₂ / 1 h / Ambient temperature

With 1H-imidazole; dmap; iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; triethylamine; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja9725864