(5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane

Base Information

Chemical Name:(5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane
CAS No.:474125-25-2
Molecular Formula:C₂₄H₃₆O₅
Molecular Weight:404.547
Hs Code.:

Synonyms:(5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane

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Chemical Property of (5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane

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Technology Process of (5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane

There total 16 articles about (5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane 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%

: 100-39-0
benzyl bromide

: 253172-19-9
(1S,2R)-1-((5R,7S,8R,9S,10S)-8-Methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-2-methyl-but-3-en-1-ol

: 474125-25-2
(5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1039/a906834a

Reference yield:

: 253172-18-8
((5R,7S,8R,9S,10S)-8-Methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]dec-7-yl)-methanol

: 474125-25-2
(5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane

Guidance literature:: Multi-step reaction with 3 steps

1: DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 2.25 h / -80 - -60 °C

2: 4.8 g / toluene / 0.58 h / -80 - -70 °C

3: 3.79 g / NaH / tetrahydrofuran; dimethylformamide / 7 h / 20 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00660-9

Reference yield:

: (E)-(R)-6-Benzyloxy-2,3-dimethyl-hex-4-enoic acid

: 474125-25-2
(5R,7S,8R,9S,10S)-7-((1S,2R)-1-Benzyloxy-2-methyl-but-3-enyl)-8-methoxymethoxy-9,10-dimethyl-1,6-dioxa-spiro[4.5]decane

Guidance literature:: Multi-step reaction with 11 steps

1.1: 24.8 g / ethyl acetate / 0 - 20 °C

2.1: 62 percent / I₂ / acetonitrile / 0 - 20 °C

3.1: aq. NaOH / ethanol / 2 h / 20 °C

3.2: 72 percent / AcOH / ethanol / 1 h / 60 °C

4.1: 95 percent / N,N-diisopropylethylamine / 1,2-dichloro-ethane / 24 h / 50 °C

5.1: tetrahydrofuran / 1.17 h / -70 °C

6.1: disiamylborane / tetrahydrofuran / 1.17 h / 0 °C

6.2: H₂O₂; NaHCO₃ / tetrahydrofuran; methanol; H₂O / 20 °C

7.1: 37.5 g / 10-camphorsulfonic acid / 1,2-dichloro-ethane / 3 h / 20 °C

8.1: 100 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 24 h / 20 °C

9.1: DMSO; (COCl)2; triethylamine / CH₂Cl₂ / 2.25 h / -80 - -60 °C

10.1: 4.8 g / toluene / 0.58 h / -80 - -70 °C

11.1: 3.79 g / NaH / tetrahydrofuran; dimethylformamide / 7 h / 20 °C

With sodium hydroxide; oxalyl dichloride; (1S)-10-camphorsulfonic acid; hydrogen; iodine; bis-(1,2-dimethylpropyl)borane; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; 9.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00660-9