(R)-6-Benzyloxymethoxy-6-((2S,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexanoic acid methyl ester

Base Information

Chemical Name:(R)-6-Benzyloxymethoxy-6-((2S,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexanoic acid methyl ester
CAS No.:201472-29-9
Molecular Formula:C₂₀H₃₀O₆
Molecular Weight:366.455
Hs Code.:

Synonyms:(R)-6-Benzyloxymethoxy-6-((2S,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexanoic acid methyl ester

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Chemical Property of (R)-6-Benzyloxymethoxy-6-((2S,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexanoic acid methyl ester

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Technology Process of (R)-6-Benzyloxymethoxy-6-((2S,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexanoic acid methyl ester

There total 10 articles about (R)-6-Benzyloxymethoxy-6-((2S,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexanoic acid methyl ester 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:

: 102717-29-3
(5S)-5-({[tert-butyl(diphenyl)silyl]oxy}methyl)dihydrofuran-2(3H)-one

: 201472-29-9
(R)-6-Benzyloxymethoxy-6-((2S,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / DIBAL-H / toluene / 1 h / -78 °C

2: 1.) Ac₂O, DMAP, TEA, 2.) BF₃*OEt₂ / 1) CH₂Cl₂, rt, 1 h; 2) CH₂Cl₂, -78 deg C, 1 h

3: 92 percent / H₂ / Pd/C / ethyl acetate / 5 h / 760 Torr

4: 94 percent / DIBAL-H / toluene / 1 h / -78 °C

5: 85 percent / PhCO₂H / CH₂Cl₂ / 12 h / Ambient temperature

6: 1.5 g / H₂ / Pd/C / ethyl acetate / 5 h / Ambient temperature

7: 65 percent / DIPEA / CH₂Cl₂ / 48 h / 0 °C

8: 0.5 g / n-BuNF / tetrahydrofuran / 3 h / Ambient temperature

With dmap; TEA; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo9713621

Reference yield:

: 201472-26-6
(2R/S,5S)-5-(tert-butyldiphenylsilyloxymethyl)tetrahydrofuran-2-ol

: 201472-29-9
(R)-6-Benzyloxymethoxy-6-((2S,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) Ac₂O, DMAP, TEA, 2.) BF₃*OEt₂ / 1) CH₂Cl₂, rt, 1 h; 2) CH₂Cl₂, -78 deg C, 1 h

2: 92 percent / H₂ / Pd/C / ethyl acetate / 5 h / 760 Torr

3: 94 percent / DIBAL-H / toluene / 1 h / -78 °C

4: 85 percent / PhCO₂H / CH₂Cl₂ / 12 h / Ambient temperature

5: 1.5 g / H₂ / Pd/C / ethyl acetate / 5 h / Ambient temperature

6: 65 percent / DIPEA / CH₂Cl₂ / 48 h / 0 °C

7: 0.5 g / n-BuNF / tetrahydrofuran / 3 h / Ambient temperature

With dmap; TEA; boron trifluoride diethyl etherate; hydrogen; acetic anhydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; benzoic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo9713621

Reference yield:

: 157810-24-7
(2S,2'S,5'S)-5'-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-[2,2']bifuranyl-5-one

: 201472-29-9
(R)-6-Benzyloxymethoxy-6-((2S,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) LiOH, 2.) Ph₃P, DEAD / 1) THF, H₂O, 0 deg C, 1 h; 2) THF, 0 deg C, 30 min

2: 94 percent / DIBAL-H / toluene / 1 h / -78 °C

3: 85 percent / PhCO₂H / CH₂Cl₂ / 12 h / Ambient temperature

4: 1.5 g / H₂ / Pd/C / ethyl acetate / 5 h / Ambient temperature

5: 65 percent / DIPEA / CH₂Cl₂ / 48 h / 0 °C

6: 0.5 g / n-BuNF / tetrahydrofuran / 3 h / Ambient temperature

With lithium hydroxide; hydrogen; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; benzoic acid; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo9713621