(S)-5-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2,4,4-tetramethyl-[1,3]dioxolane

Base Information

Chemical Name:(S)-5-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2,4,4-tetramethyl-[1,3]dioxolane
CAS No.:434342-76-4
Molecular Formula:C₃₂H₄₄O₆
Molecular Weight:524.698
Hs Code.:

Synonyms:(S)-5-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2,4,4-tetramethyl-[1,3]dioxolane

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Chemical Property of (S)-5-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2,4,4-tetramethyl-[1,3]dioxolane

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Technology Process of (S)-5-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2,4,4-tetramethyl-[1,3]dioxolane

There total 7 articles about (S)-5-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2,4,4-tetramethyl-[1,3]dioxolane 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: 84.0%

: 100-39-0
benzyl bromide

: 434342-89-9
(1S,2S,4R,5R,6R)-5-Hydroxymethyl-4-methoxymethoxy-5-methyl-6-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]heptan-2-ol

: 434342-76-4
(S)-5-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2,4,4-tetramethyl-[1,3]dioxolane

Guidance literature:: With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1055/s-2002-19778

Reference yield:

: 106268-98-8
(S)-(3,3-dimethyloxiran-2-yl)methyl 4-nitrobenzoate

: 434342-76-4
(S)-5-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2,4,4-tetramethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 7 steps

1: 97 percent / H₂SO₄ / benzene / 0 - 20 °C

2: 81 percent / K₂CO₃ / ethanol / 20 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

4: benzene / 20 °C

5: 62 percent / LDA / tetrahydrofuran / -78 °C

6: 99 percent / DIBALH / tetrahydrofuran / -78 °C

7: 84 percent / NaH / tetrahydrofuran; dimethylformamide / 20 °C

With oxalyl dichloride; sulfuric acid; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 5: Michael reaction;
DOI:10.1055/s-2002-19778

Reference yield:

: 37504-92-0
(4'S)-(2',2',5',5'-tetramethyl-1',3'-dioxolan-4'-yl)methanol

: 434342-76-4
(S)-5-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2,2,4,4-tetramethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 5 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2: benzene / 20 °C

3: 62 percent / LDA / tetrahydrofuran / -78 °C

4: 99 percent / DIBALH / tetrahydrofuran / -78 °C

5: 84 percent / NaH / tetrahydrofuran; dimethylformamide / 20 °C

With oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene; 3: Michael reaction;
DOI:10.1055/s-2002-19778