(E)-(R)-6-((2S,4R,6S,8S,9R)-4-Benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2,4-dimethyl-hex-4-enoic acid

Base Information

Chemical Name:(E)-(R)-6-((2S,4R,6S,8S,9R)-4-Benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2,4-dimethyl-hex-4-enoic acid
CAS No.:82109-86-2
Molecular Formula:C₂₆H₃₈O₅
Molecular Weight:430.585
Hs Code.:

Synonyms:(E)-(R)-6-((2S,4R,6S,8S,9R)-4-Benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2,4-dimethyl-hex-4-enoic acid

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Chemical Property of (E)-(R)-6-((2S,4R,6S,8S,9R)-4-Benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2,4-dimethyl-hex-4-enoic acid

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Technology Process of (E)-(R)-6-((2S,4R,6S,8S,9R)-4-Benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2,4-dimethyl-hex-4-enoic acid

There total 11 articles about (E)-(R)-6-((2S,4R,6S,8S,9R)-4-Benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2,4-dimethyl-hex-4-enoic acid 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: 57.0%

: 82045-49-6
Propionic acid (S)-1-((2S,4S,6R,8R,9S)-4-benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-ylmethyl)-2-methyl-allyl ester

: 82109-86-2
(E)-(R)-6-((2S,4R,6S,8S,9R)-4-Benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2,4-dimethyl-hex-4-enoic acid

Guidance literature:: With chloro-trimethyl-silane; potassium hexamethylsilazane; at -78 - 25 ℃;
DOI:10.1021/ja00378a045

Reference yield:

: 82045-40-7
trans‐5‐methyl‐6‐methyltetrahydro‐2H‐pyran‐2‐one

: 82109-86-2
(E)-(R)-6-((2S,4R,6S,8S,9R)-4-Benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2,4-dimethyl-hex-4-enoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 2.) CeCl₃*7H₂O / 1.) THF, -78 deg C, 3 h; 2.) 16 h

2: triethylamine, methyl isocyanate / benzene / 48 h / 75 °C

3: LAH / diethyl ether / 3 h / Heating

4: 1.) KH; 2.) MeI; 3.) TsOH / 1.) THF, r.t., 3 h; 2.) THF, r.t., 48 h; 3.) THF, 25 deg C, 24 h

5: 1.) CuBr*DMS, benzaldehyde; 2.) pyridine, DMAP / 1.) DMS, Et₂O, -78 deg C, 20 min; 2.) CH₂Cl₂, 0 deg C, 1 h

6: 1.) KN(SiMe₃)2, HMPA; 2.) Me₃SiCl*TEA / 1.) THF, -78 deg C, 10 min; 2.) THF, 25 deg C, 1 h then 40-50 deg C, 1 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; TEA; potassium hydride; potassium hexamethylsilazane; benzaldehyde; toluene-4-sulfonic acid; triethylamine; methyl isocyanate; methyl iodide; cerium(III) chloride; In diethyl ether; benzene;
DOI:10.1021/ja00270a027

Reference yield:

: 82045-44-1
(2S,5R,6S)-2-Allyl-2-methoxy-5,6-dimethyl-tetrahydro-pyran

: 82109-86-2
(E)-(R)-6-((2S,4R,6S,8S,9R)-4-Benzyloxy-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl)-2,4-dimethyl-hex-4-enoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: triethylamine, methyl isocyanate / benzene / 48 h / 75 °C

2: LAH / diethyl ether / 3 h / Heating

3: 1.) KH; 2.) MeI; 3.) TsOH / 1.) THF, r.t., 3 h; 2.) THF, r.t., 48 h; 3.) THF, 25 deg C, 24 h

4: 1.) CuBr*DMS, benzaldehyde; 2.) pyridine, DMAP / 1.) DMS, Et₂O, -78 deg C, 20 min; 2.) CH₂Cl₂, 0 deg C, 1 h

5: 1.) KN(SiMe₃)2, HMPA; 2.) Me₃SiCl*TEA / 1.) THF, -78 deg C, 10 min; 2.) THF, 25 deg C, 1 h then 40-50 deg C, 1 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; TEA; potassium hydride; potassium hexamethylsilazane; benzaldehyde; toluene-4-sulfonic acid; triethylamine; methyl isocyanate; methyl iodide; In diethyl ether; benzene;
DOI:10.1021/ja00270a027