(R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one

Base Information

Chemical Name:(R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one
CAS No.:137769-66-5
Molecular Formula:C₂₇H₃₆O₈
Molecular Weight:488.578
Hs Code.:

Synonyms:(R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one

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Chemical Property of (R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one

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Technology Process of (R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one

There total 10 articles about (R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one 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:

: 137769-52-9
(2R,4R)-4-(2-Bromo-allyl)-2-tert-butyl-4-methyl-5-methylene-[1,3]dioxolane

: 137769-66-5
(R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one

Guidance literature:: Multi-step reaction with 9 steps

2: 98 percent / DBU / CH₂Cl₂ / 12 h / Heating

3: 80 percent / BF₃*Et₂O / 0.67 h / -78 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5: 5percent aq. HCl / tetrahydrofuran / 8 h / 25 °C

6: 93 percent / OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 12 h / 25 °C

7: NaBH₄ / methanol / 0.25 h / -40 °C

8: 81 percent / P₂O₅, molecular sieves / CH₂Cl₂ / 0.67 h / 25 °C

9: 1.) LDA / 1.) THF, -78 deg C, 40 min, 2.) THF, -78 deg C, 1.5 h

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; molecular sieve; boron trifluoride diethyl etherate; phosphorus pentoxide; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ja00025a049

Reference yield:

: 137769-53-0
(2S,5R)-5-(2-Bromo-allyl)-2-tert-butyl-5-methyl-[1,3]dioxolan-4-one

: 137769-66-5
(R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one

Guidance literature:: Multi-step reaction with 10 steps

1: 83 percent / tetrahydrofuran; toluene / 1.) from 0 deg C to 25 deg C, 4 h, 2.) 25 deg C, 10 h

3: 98 percent / DBU / CH₂Cl₂ / 12 h / Heating

4: 80 percent / BF₃*Et₂O / 0.67 h / -78 °C

5: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6: 5percent aq. HCl / tetrahydrofuran / 8 h / 25 °C

7: 93 percent / OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 12 h / 25 °C

8: NaBH₄ / methanol / 0.25 h / -40 °C

9: 81 percent / P₂O₅, molecular sieves / CH₂Cl₂ / 0.67 h / 25 °C

10: 1.) LDA / 1.) THF, -78 deg C, 40 min, 2.) THF, -78 deg C, 1.5 h

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; molecular sieve; boron trifluoride diethyl etherate; phosphorus pentoxide; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1021/ja00025a049

Reference yield:

: (4R,5S)-5-Benzyloxy-4-[1-((2R,4R)-2-tert-butyl-4-methyl-5-methylene-[1,3]dioxolan-4-ylmethyl)-vinyl]-dihydro-furan-2-one

: 137769-66-5
(R)-2-[(S)-2-((2S,3R,4R)-2-Benzyloxymethyl-4-isobutyryl-5-oxo-tetrahydro-furan-3-yl)-2-methoxymethoxy-ethyl]-5-ethyl-2-methyl-furan-3-one

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / DBU / CH₂Cl₂ / 12 h / Heating

2: 80 percent / BF₃*Et₂O / 0.67 h / -78 °C

3: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4: 5percent aq. HCl / tetrahydrofuran / 8 h / 25 °C

5: 93 percent / OsO₄, NaIO₄ / tetrahydrofuran; H₂O / 12 h / 25 °C

6: NaBH₄ / methanol / 0.25 h / -40 °C

7: 81 percent / P₂O₅, molecular sieves / CH₂Cl₂ / 0.67 h / 25 °C

8: 1.) LDA / 1.) THF, -78 deg C, 40 min, 2.) THF, -78 deg C, 1.5 h

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; molecular sieve; boron trifluoride diethyl etherate; phosphorus pentoxide; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1021/ja00025a049