(3S,4S,5R)-3-benzyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methoxymethoxymethyl-2-dihydrofuranone

Base Information

Chemical Name:(3S,4S,5R)-3-benzyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methoxymethoxymethyl-2-dihydrofuranone
CAS No.:862107-68-4
Molecular Formula:C₃₂H₄₀O₆Si
Molecular Weight:548.751
Hs Code.:

Synonyms:(3S,4S,5R)-3-benzyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methoxymethoxymethyl-2-dihydrofuranone

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Chemical Property of (3S,4S,5R)-3-benzyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methoxymethoxymethyl-2-dihydrofuranone

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Technology Process of (3S,4S,5R)-3-benzyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methoxymethoxymethyl-2-dihydrofuranone

There total 5 articles about (3S,4S,5R)-3-benzyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methoxymethoxymethyl-2-dihydrofuranone 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:

: 862107-67-3
(3S,4R)-3-Benzyloxy-5-[2-(tert-butyl-diphenyl-silanyloxy)-1-iodo-ethyl]-4-methoxymethoxymethyl-dihydro-furan-2-one

: 862107-68-4
(3S,4S,5R)-3-benzyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methoxymethoxymethyl-2-dihydrofuranone

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 95 ℃; for 1h;
DOI:10.1021/ol050578j

Reference yield:

: 862107-71-9
(2S)-(tert-butyldimethylsilanyloxymethyl)-1-[(1R)-1-(tert-butyldiphenylsilanyloxymethyl)-4-methoxymethoxy-2-butynyl]pyrrolidine

: 862107-68-4
(3S,4S,5R)-3-benzyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methoxymethoxymethyl-2-dihydrofuranone

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / H₂ / Lindlar catalyst / ethyl acetate / 1 h / 20 °C

2: 64 percent / Zn(OSO₂CF₃)2; i-Pr₂NEt / CH₂Cl₂ / 0 °C

3: I₂ / tetrahydrofuran; H₂O / 4 h / 0 °C

4: 97 mg / AIBN; Bu₃SnH / toluene / 1 h / 95 °C

With 2,2'-azobis(isobutyronitrile); hydrogen; iodine; tri-n-butyl-tin hydride; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene;
DOI:10.1021/ol050578j

Reference yield:

: 17869-81-7
methoxy(prop-2-yn-1-yloxy)methane

: 862107-68-4
(3S,4S,5R)-3-benzyloxy-5-[2-(tert-butyldiphenylsilanyloxy)ethyl]-4-methoxymethoxymethyl-2-dihydrofuranone

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / CuBr; molecular sieves 4 Angstroem / toluene / 20 h / 20 °C

2: 100 percent / H₂ / Lindlar catalyst / ethyl acetate / 1 h / 20 °C

3: 64 percent / Zn(OSO₂CF₃)2; i-Pr₂NEt / CH₂Cl₂ / 0 °C

4: I₂ / tetrahydrofuran; H₂O / 4 h / 0 °C

5: 97 mg / AIBN; Bu₃SnH / toluene / 1 h / 95 °C

With 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; hydrogen; iodine; tri-n-butyl-tin hydride; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; copper(I) bromide; Lindlar's catalyst; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene;
DOI:10.1021/ol050578j