Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-acetylamino-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-methoxymethoxy-pentyl ester

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Chemical Name:Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-acetylamino-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-methoxymethoxy-pentyl ester
CAS No.:677334-84-8
Molecular Formula:C₂₁H₃₃NO₁₀S
Molecular Weight:491.56
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-acetylamino-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-methoxymethoxy-pentyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-acetylamino-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-methoxymethoxy-pentyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-acetylamino-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-methoxymethoxy-pentyl ester

There total 7 articles about Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-acetylamino-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-methoxymethoxy-pentyl 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: 79.0%

: 98-59-9
p-toluenesulfonyl chloride

: 677334-91-7
N-[(1R,2R,3S,4R)-1-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,3,5-trihydroxy-4-methoxymethoxy-pentyl]-acetamide

: 677334-84-8
Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-acetylamino-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-methoxymethoxy-pentyl ester

Guidance literature:: With di(n-butyl)tin oxide; triethylamine; In dichloromethane;
DOI:10.1016/j.tetlet.2003.12.135

Reference yield:

: 157831-25-9
(2R,3R,4R,5S)-1,3,4-Tris-benzyloxy-5-(4-methoxy-benzylamino)-hept-6-en-2-ol

: 677334-84-8
Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-acetylamino-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-methoxymethoxy-pentyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: CH₂Cl₂

1.2: 50 percent / K₂CO₃ / methanol

2.1: 49 percent / CAN / methanol

3.1: 99 percent / OsO₄; NMO / acetone; H₂O

4.1: 90 percent / p-TsOH / acetone

5.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂

6.1: 97 percent / H₂ / Pd/C / methanol

7.1: 79 percent / Bu₂SnO; Et₃N / CH₂Cl₂

With osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; hydrogen; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; water; acetone;
DOI:10.1016/j.tetlet.2003.12.135

Reference yield:

: 677334-92-8
N-[(1S,2R,3R,4R)-2,3,5-Tris-benzyloxy-1-(1,2-dihydroxy-ethyl)-4-hydroxy-pentyl]-acetamide

: 677334-84-8
Toluene-4-sulfonic acid (2R,3S,4R,5R)-5-acetylamino-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-2-methoxymethoxy-pentyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / p-TsOH / acetone

2: 94 percent / (i-Pr)2NEt / CH₂Cl₂

3: 97 percent / H₂ / Pd/C / methanol

4: 79 percent / Bu₂SnO; Et₃N / CH₂Cl₂

With hydrogen; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; dichloromethane; acetone;
DOI:10.1016/j.tetlet.2003.12.135