5(S),8(S)-dibenzoyloxy-1,12-ditetrahydropyranyloxy-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol

Base Information

• Chemical Name: 5(S),8(S)-dibenzoyloxy-1,12-ditetrahydropyranyloxy-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol
• CAS No.: 121525-70-0
• Molecular Formula: C₃₉H₄₆O₁₀
• Molecular Weight: 674.788

Synonyms:5(S),8(S)-dibenzoyloxy-1,12-ditetrahydropyranyloxy-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol

Chemical Property of 5(S),8(S)-dibenzoyloxy-1,12-ditetrahydropyranyloxy-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol

Chemical Property:

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Technology Process of 5(S),8(S)-dibenzoyloxy-1,12-ditetrahydropyranyloxy-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol

There total 2 articles about 5(S),8(S)-dibenzoyloxy-1,12-ditetrahydropyranyloxy-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol 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:

3-(tetrahydropyran-2'-yloxy)propyne (6089-04-9) + benzoyl chloride (98-88-4) + 1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol (63699-97-8) → 5(S),8(S)-dibenzoyloxy-1,12-ditetrahydropyranyloxy-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol (121525-70-0)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF/hexane/HMPA, reflux, 20 h; 2.)THF/hexane/HMPA, r.t., 1 h;

DOI:10.1016/S0040-4020(01)89193-6

Reference yield:

(3-tetrahydropyran-2-yloxy-prop-1-ynyl)-lithium (37566-51-1) + benzoyl chloride (98-88-4) + 1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol (63699-97-8) → 5(S),8(S)-dibenzoyloxy-1,12-ditetrahydropyranyloxy-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol (121525-70-0)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; Yield given. Multistep reaction; 1) THF, 20h, reflux, 2) 0 deg C;

Reference yield: 70.0%

5(S),8(S)-dibenzoyloxy-1,12-ditetrahydropyranyloxy-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol (121525-70-0) → 5(S),8(S)-dibenzoyloxy-1,12-dibromo-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol (121525-71-1)

Guidance literature:

With temephos; bromine; In dichloromethane; at 25 ℃; for 1.5h;

DOI:10.1016/S0040-4020(01)89193-6

upstream raw materials:

3-(tetrahydropyran-2'-yloxy)propyne

benzoyl chloride

1,2:5,6-dianhydro-3,4-O-methylethylidene-L-iditol

(3-tetrahydropyran-2-yloxy-prop-1-ynyl)-lithium

Downstream raw materials:

5(S),8(S)-dibenzoyloxy-1,12-dibromo-6(R),7(R)-O-methylethylidene-2,10-dodecadiyn-6,7-diol

12(S),15(S)-dibenzoyloxy-13(R),14(R)-O-methylethylidene-6,9,17,20-hexaeicosatetrayn-13,14-diol

2(S)-benzoyloxy-4(Z),7(Z)-tridecadienal

4(S)-benzoyloxy-2(E),6(Z),9(Z)-pentadecatrienal

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