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

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Chemical Name:benzyl 2(S)-<5(R)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether
CAS No.:84985-05-7
Molecular Formula:C₂₆H₃₈O₇
Molecular Weight:462.584
Hs Code.:

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

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Chemical Property of benzyl 2(S)-<5(R)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether

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Technology Process of benzyl 2(S)-<5(R)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether

There total 2 articles about benzyl 2(S)-<5(R)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether 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:

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 84911-94-4
1,5-anhydro-2,6-dideoxy-4-O-(methoxymethyl)-L-xylo-hex-1-enitol

: 73657-47-3,84984-96-3,87598-94-5
(2S,4S,5S)-5-((R)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carboxylic acid

: 84985-04-6
benzyl 2(R)-<5(S)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether

: 84911-83-1,84985-04-6,84985-05-7,84985-06-8,87678-28-2,87678-29-3
benzyl 2(R)-<5(R)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether

Guidance literature:: Yield given. Multistep reaction. Yields of byproduct given;
DOI:10.1021/ja00345a055

Reference yield:

: 186581-53-3,908094-01-9,334-88-3
diazomethane

: 84911-94-4
1,5-anhydro-2,6-dideoxy-4-O-(methoxymethyl)-L-xylo-hex-1-enitol

: 73657-47-3,84984-96-3,87598-94-5
(2S,4S,5S)-5-((S)-1-Benzyloxymethyl-propyl)-4-methyl-tetrahydro-furan-2-carboxylic acid

: 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

: 84985-05-7
benzyl 2(S)-<5(R)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether

Guidance literature:: Yield given. Multistep reaction. Yields of byproduct given;
DOI:10.1021/ja00345a055

Reference yield:

: 84911-83-1,84985-04-6,84985-05-7,84985-06-8,87678-28-2,87678-29-3
benzyl 2(R)-<5(R)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether

: 84985-19-3
benzyl 2(R)-<5(R)-ethyl-3(S)-methyl-5-(5(S)-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether

Guidance literature:: Multi-step reaction with 5 steps

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

2: 96 percent / DIBAL / diethyl ether; hexane / 1 h / -78 °C

3: 80 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: 97 percent / 10percent HCl / tetrahydrofuran; H₂O / 16 h / 50 °C

With hydrogenchloride; n-butyllithium; hydrogen; diisobutylaluminium hydride; Ni(Ra); In tetrahydrofuran; diethyl ether; hexane; water; ethyl acetate;
DOI:10.1021/ja00345a055