Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4R,5R,6S)-5-benzenesulfonylamino-2-benzyloxymethyl-6-ethylsulfanyl-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,4R,5R,6S)-5-benzenesulfonylamino-2-benzyloxymethyl-6-ethylsulfanyl-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester
CAS No.:202657-39-4
Molecular Formula:C₄₃H₅₇NO₁₃S₂Si
Molecular Weight:888.142
Hs Code.:

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

There total 11 articles about Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4R,5R,6S)-5-benzenesulfonylamino-2-benzyloxymethyl-6-ethylsulfanyl-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: 91.0%

: 75-08-1
ethanethiol

: 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

: 202657-39-4
Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4R,5R,6S)-5-benzenesulfonylamino-2-benzyloxymethyl-6-ethylsulfanyl-4-triethylsilanyloxy-tetrahydro-pyran-3-yloxy)-4-benzyloxymethyl-2-oxo-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at -40 ℃; for 1h;
DOI:10.1021/ja9725864

Reference yield:

: 100-39-0
benzyl bromide

: 202657-39-4
Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4R,5R,6S)-5-benzenesulfonylamino-2-benzyloxymethyl-6-ethylsulfanyl-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 6 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

6: 91 percent / LHMDS / dimethylformamide; tetrahydrofuran / 1 h / -40 °C

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

Reference yield:

: 994-30-9
triethylsilyl chloride

: 202657-39-4
Acetic acid (3aS,4R,6S,7R,7aS)-6-((2R,3R,4R,5R,6S)-5-benzenesulfonylamino-2-benzyloxymethyl-6-ethylsulfanyl-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: 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

5: 91 percent / LHMDS / dimethylformamide; tetrahydrofuran / 1 h / -40 °C

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