(3S,4R,6S)-6-[(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-4-methyl-1,5-dioxa-spiro[2.5]octane

Base Information

Chemical Name:(3S,4R,6S)-6-[(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-4-methyl-1,5-dioxa-spiro[2.5]octane
CAS No.:87678-39-5
Molecular Formula:C₂₅H₃₈O₄
Molecular Weight:402.574
Hs Code.:

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Chemical Property of (3S,4R,6S)-6-[(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-4-methyl-1,5-dioxa-spiro[2.5]octane

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Technology Process of (3S,4R,6S)-6-[(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-4-methyl-1,5-dioxa-spiro[2.5]octane

There total 8 articles about (3S,4R,6S)-6-[(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-4-methyl-1,5-dioxa-spiro[2.5]octane 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:

: 87678-33-9
benzyl 2(R)-<5(S)-vinyl-3(R)-methyl-5-<5(R)-(methoxymethoxy)-6(R)-methyl-2(S)-tetrahydropyranyl>-2(R)-tetrahydrofuryl>butyl ether

: 87678-39-5
(3S,4R,6S)-6-[(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-4-methyl-1,5-dioxa-spiro[2.5]octane

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / H₂ / W-2 Raney nickel catalyst / ethyl acetate / 12 h

2: 10percent aq. HCl / tetrahydrofuran / 12 h / 50 °C

3: 99 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 0.25 h / -60 °C

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

5: solid NaHCO₃, 80-90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.) 0 deg C, 2.) room temp., 3 h

With hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; W-2 Raney nickel catalyst; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jo00174a008

Reference yield:

: 87678-32-8
benzyl 2(R)-<5(R)-formyl-3(R)-methyl-5-<5(R)-(methoxymethoxy)-6(R)-methyl-2(S)-tetrahydropyranyl>-2(R)-tetrahydrofuryl>butyl ether

: 87678-39-5
(3S,4R,6S)-6-[(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-4-methyl-1,5-dioxa-spiro[2.5]octane

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

2: 97 percent / H₂ / W-2 Raney nickel catalyst / ethyl acetate / 12 h

3: 10percent aq. HCl / tetrahydrofuran / 12 h / 50 °C

4: 99 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 0.25 h / -60 °C

5: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

6: solid NaHCO₃, 80-90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.) 0 deg C, 2.) room temp., 3 h

With hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; W-2 Raney nickel catalyst; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1021/jo00174a008

Reference yield:

: 87678-31-7
benzyl 2(R)-<5(R)-carbomethoxy-3(R)-methyl-5-<5(R)-(methoxymethoxy)-6(R)-methyl-2(S)-tetrahydropyranyl>-2(R)-tetrahydrofuryl>butyl ether

: 87678-39-5
(3S,4R,6S)-6-[(2R,4R,5R)-5-((R)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-4-methyl-1,5-dioxa-spiro[2.5]octane

Guidance literature:: Multi-step reaction with 7 steps

1: 89 percent / 1M diisobutylaluminum hydride / diethyl ether; methanol / 1 h / -78 °C

2: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

3: 97 percent / H₂ / W-2 Raney nickel catalyst / ethyl acetate / 12 h

4: 10percent aq. HCl / tetrahydrofuran / 12 h / 50 °C

5: 99 percent / oxalyl chloride, dimethyl sulfoxide, triethylamine / CH₂Cl₂ / 0.25 h / -60 °C

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, then room temp., 1 h, 2.) THF, -78 deg C, then room temp., 10 h

7: solid NaHCO₃, 80-90percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.) 0 deg C, 2.) room temp., 3 h

With hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; W-2 Raney nickel catalyst; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/jo00174a008