3,6-di-O-benzyl-(-)-allosamizoline

Base Information

Chemical Name:3,6-di-O-benzyl-(-)-allosamizoline
CAS No.:134756-66-4
Molecular Formula:C₂₃H₂₈N₂O₄
Molecular Weight:396.486
Hs Code.:

Synonyms:3,6-di-O-benzyl-(-)-allosamizoline

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Chemical Property of 3,6-di-O-benzyl-(-)-allosamizoline

Chemical Property:

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Technology Process of 3,6-di-O-benzyl-(-)-allosamizoline

There total 22 articles about 3,6-di-O-benzyl-(-)-allosamizoline 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: 52.0%

: 100-39-0
benzyl bromide

: 252055-28-0
3-O-benzylallosamizoline

: 134756-66-4
3,6-di-O-benzyl-(-)-allosamizoline

Guidance literature:: 3-O-benzylallosamizoline; With di(n-butyl)tin oxide; In toluene; for 4h; Heating;

benzyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 24 ℃; for 16h;
DOI:10.1016/S0957-4166(00)00156-7

Reference yield:

: 100021-11-2
(1α,2β,3α)-2-(benzyloxymethyl)cyclopent-4-ene-1,3-diol

: 134756-66-4
3,6-di-O-benzyl-(-)-allosamizoline

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / triethylamine, DMAP / CH₂Cl₂ / 1 h

2: 95 percent / NaH₂PO₄ buffer, aq. sodium azide / 144 h / electric eel acetylcholinesterase

3: imidazole / 0.5 h

4: methanolic ammonia / 48 h

5: pyridine / CH₂Cl₂ / 0.25 h

6: methanolic ammonia / 15 h

7: 91 percent / HF / acetonitrile / 9 h

8: 63 percent / triethylamine, trifluoroacetic anhydride / tetrahydrofuran / 4 h / -78 - 20 °C

9: 1.) methyl trifluoromethanesulfonate / 1.) CH₂Cl₂, 5 h, 2.) RT, 2 d

10: 44 percent / trifluoroperacetic acid / CH₂Cl₂ / 2 h

11: 1.) dibutyltin oxide, 2.) CsF / 1.) methanol, reflux, 1 h, 2.) DMF, 12 h

With pyridine; 1H-imidazole; dmap; sodium azide; trifluoroacetyl peroxide; NaH₂PO₄ buffer; hydrogen fluoride; ammonia; di(n-butyl)tin oxide; triethylamine; cesium fluoride; trifluoroacetic anhydride; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ja960526c

Reference yield:

: 134756-65-3
<1(R)-(1α,2β,3α)>-2-<(benzyloxy)methyl>-4-cyclopentene-1,3-diol monocarbamate

: 134756-66-4
3,6-di-O-benzyl-(-)-allosamizoline

Guidance literature:: Multi-step reaction with 4 steps

1: 63 percent / triethylamine, trifluoroacetic anhydride / tetrahydrofuran / 4 h / -78 - 20 °C

2: 1.) methyl trifluoromethanesulfonate / 1.) CH₂Cl₂, 5 h, 2.) RT, 2 d

3: 44 percent / trifluoroperacetic acid / CH₂Cl₂ / 2 h

4: 1.) dibutyltin oxide, 2.) CsF / 1.) methanol, reflux, 1 h, 2.) DMF, 12 h

With trifluoroacetyl peroxide; di(n-butyl)tin oxide; triethylamine; cesium fluoride; trifluoroacetic anhydride; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja960526c