(3S,6R,9S)-3-benzyloxymethyl-9-(p-tosyl)oxymethyl-1,7-dioxaspiro<5.5>undec-4-ene

Base Information

• Chemical Name: (3S,6R,9S)-3-benzyloxymethyl-9-(p-tosyl)oxymethyl-1,7-dioxaspiro<5.5>undec-4-ene
• CAS No.: 113457-92-4
• Molecular Formula: C₂₅H₃₀O₆S
• Molecular Weight: 458.576
• Mol file: 113457-92-4.mol

Synonyms:(3S,6R,9S)-3-benzyloxymethyl-9-(p-tosyl)oxymethyl-1,7-dioxaspiro<5.5>undec-4-ene

Chemical Property of (3S,6R,9S)-3-benzyloxymethyl-9-(p-tosyl)oxymethyl-1,7-dioxaspiro<5.5>undec-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,6R,9S)-3-benzyloxymethyl-9-(p-tosyl)oxymethyl-1,7-dioxaspiro<5.5>undec-4-ene

There total 14 articles about (3S,6R,9S)-3-benzyloxymethyl-9-(p-tosyl)oxymethyl-1,7-dioxaspiro<5.5>undec-4-ene 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: 89.0%

Toluene-4-sulfonic acid (3S,6S,9S,11S)-9-benzyloxymethyl-11-((R)-toluene-4-sulfinyl)-1,7-dioxa-spiro[5.5]undec-3-ylmethyl ester → (3S,6R,9S)-3-benzyloxymethyl-9-(p-tosyl)oxymethyl-1,7-dioxaspiro<5.5>undec-4-ene (113457-92-4)

Guidance literature:

With phosphorous acid trimethyl ester; In toluene; at 150 ℃; for 8h;

DOI:10.1248/cpb.41.946

Reference yield:

diethyl 2-(3-oxo-propyl)malonate (19515-61-8) → (3S,6R,9S)-3-benzyloxymethyl-9-(p-tosyl)oxymethyl-1,7-dioxaspiro<5.5>undec-4-ene (113457-92-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) H⁽¹⁺⁾; 2.) LAH / 2.) ether

2: 1.)imidazole; 2.) p-TsOH / 2.) acetone

3: 84 percent

4: 87 percent

6: 91 percent / ZnCl₂

7: 71 percent / trifluoroacetic acid

8: (n-Bu)4NF / tetrahydrofuran / Ambient temperature

9: KH / tetrahydrofuran / Ambient temperature

10: 1.) DMAP, pyridine; 2.) P(OMe)3 / 2.) toluene

With pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen cation; potassium hydride; toluene-4-sulfonic acid; trifluoroacetic acid; zinc(II) chloride; phosphorous acid trimethyl ester; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96304-4

Reference yield:

benzyl bromide (100-39-0) → (3S,6R,9S)-3-benzyloxymethyl-9-(p-tosyl)oxymethyl-1,7-dioxaspiro<5.5>undec-4-ene (113457-92-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / trifluoroacetic acid

2: (n-Bu)4NF / tetrahydrofuran / Ambient temperature

3: KH / tetrahydrofuran / Ambient temperature

4: 1.) DMAP, pyridine; 2.) P(OMe)3 / 2.) toluene

With pyridine; dmap; tetrabutyl ammonium fluoride; potassium hydride; trifluoroacetic acid; phosphorous acid trimethyl ester; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)96304-4

upstream raw materials:

(3S,5S,6R,9R,R_S)-3-benzyloxymethyl-9-hydroxymethyl-5-(p-tolyl)sulfinyl-1,7-dioxaspiro<5.5>undecane

p-toluenesulfonyl chloride

diethyl 2-(3-oxo-propyl)malonate

benzyl bromide

Downstream raw materials:

(3S,6R,9R)-3-benzyloxymethyl-9-ethyl-1,7-dioxaspiro<5.5>undec-4-ene

(3S,6R,9S)-3-benzyloxymethyl-9-ethyl-1,7-dioxaspiro<5.5>undec-4-ene

(-)-Talaromycin B

(3S,6S,9S)-3-benzyloxymethyl-9-ethyl-1,7-dioxaspiro<5.5>undec-4-ene