1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

Base Information

Chemical Name:1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol
CAS No.:881185-53-1
Molecular Formula:C₃₆H₄₁NO₈S
Molecular Weight:647.789
Hs Code.:

Synonyms:1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

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Chemical Property of 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

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Technology Process of 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

There total 1 articles about 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol 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: 60.0%

: 881185-90-6
Acetic acid (2S,3R,4S)-3,4-bis-benzyloxy-5-benzyloxymethyl-5-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

: 881185-53-1
1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

: 881185-94-0
1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-L-iditol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at -78 - 20 ℃;
DOI:10.1016/j.tet.2005.11.037

Reference yield: 83.0%

: 881185-53-1
1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

: 881185-90-6
Acetic acid (2S,3R,4S)-3,4-bis-benzyloxy-5-benzyloxymethyl-5-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-ylmethyl ester

Guidance literature:: With dipyridinium dichromate; In dichloromethane; at 45 ℃; for 8h;
DOI:10.1016/j.tet.2005.11.037

Reference yield:

: 881185-53-1
1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-(p-toluenesulfonamido)-D-glucitol

: 881186-02-3
(2S,3R,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethyl-2-hydroxymethyl-N-(p-toluenesulfonamido)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / PDC / CH₂Cl₂ / 8 h / 45 °C

2: 60 percent / CeCl₃*7H₂O; NaBH₄ / methanol / -78 - 20 °C

3: 70 percent / PPh₃; DEAD / tetrahydrofuran / 0.25 h / 0 °C

4: 90 percent / Na₂CO₃ / CH₂Cl₂; methanol / 51 h / 20 °C

With sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; sodium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 3: Mitsunobu cyclization;
DOI:10.1016/j.tet.2005.11.037