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

Base Information

Chemical Name:(3R,4S,6R)-6-[(2S,4S,5S)-5-((S)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-4-methyl-1,5-dioxa-spiro[2.5]octane
CAS No.:84985-22-8
Molecular Formula:C₂₅H₃₈O₄
Molecular Weight:402.574
Hs Code.:

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

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

There total 14 articles about (3R,4S,6R)-6-[(2S,4S,5S)-5-((S)-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:

: 84985-06-8
benzyl 2(S)-<5(S)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether

: 84985-22-8
(3R,4S,6R)-6-[(2S,4S,5S)-5-((S)-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 8 steps

1: 85 percent / H₂ / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature

2: 95 percent / DIBAL / diethyl ether; hexane / 1 h / -78 °C

3: 88 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h

4: 90 percent / H₂ / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature

5: 100 percent / 10percent HCl / tetrahydrofuran; H₂O / 16 h / 50 °C

6: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et₃N / CH₂Cl₂ / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature

7: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h

8: NaHCO₃, MCPBA / CH₂Cl₂ / 3 h / Ambient temperature

With hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Ni(Ra); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate;
DOI:10.1021/ja00345a055

Reference yield:

: 84911-87-5,84985-13-7,84985-14-8,84985-15-9,87678-33-9
benzyl 2(S)-<5(R)-vinyl-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether

: 84985-22-8
(3R,4S,6R)-6-[(2S,4S,5S)-5-((S)-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: 90 percent / H₂ / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature

2: 100 percent / 10percent HCl / tetrahydrofuran; H₂O / 16 h / 50 °C

3: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et₃N / CH₂Cl₂ / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature

4: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h

5: NaHCO₃, MCPBA / CH₂Cl₂ / 3 h / Ambient temperature

With hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Ni(Ra); In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate;
DOI:10.1021/ja00345a055

Reference yield:

: 84985-12-6
benzyl 2(S)-<5(S)-formyl-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether

: 84985-22-8
(3R,4S,6R)-6-[(2S,4S,5S)-5-((S)-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: 88 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h

2: 90 percent / H₂ / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature

3: 100 percent / 10percent HCl / tetrahydrofuran; H₂O / 16 h / 50 °C

4: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et₃N / CH₂Cl₂ / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature

5: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h

6: NaHCO₃, MCPBA / CH₂Cl₂ / 3 h / Ambient temperature

With hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Ni(Ra); In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate;
DOI:10.1021/ja00345a055