(2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran

Base Information

Chemical Name:(2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran
CAS No.:529494-87-9
Molecular Formula:C₂₅H₄₄O₅Si
Molecular Weight:452.707
Hs Code.:

Synonyms:(2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran

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Chemical Property of (2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran

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Technology Process of (2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran

There total 15 articles about (2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran 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: 88.0%

: 618096-85-8
(2S,4R,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran

: 529494-87-9
(2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran

Guidance literature:: With (1S)-10-camphorsulfonic acid; In methanol; dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(03)00814-7

Reference yield:

: 193416-33-0
Triethyl-[(E)-5-(4-methoxy-benzyloxy)-1-methylene-pent-2-enyloxy]-silane

: 529494-87-9
(2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 4 Angstroem molecular sieves / (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst / 12 h / 20 °C

1.2: 80 percent / conc. HCl / CHCl₃ / 4 h

2.1: 93 percent / NaBH₄ / methanol / 1 h / 20 °C

3.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

4.1: 88 percent / 10-camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst; In methanol; dichloromethane; 1.1: hetero-Diels-Alder reaction;
DOI:10.1016/S0040-4020(03)00814-7

Reference yield:

: 193416-54-5
(E)-6-(4-methoxybenzyloxy)-1,3-hexen-2-one

: 529494-87-9
(2S,4R,6R)-tetrahydro-2-hydroxymethyl-4-(triisopropylsilyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-2H-pyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / Et₃N / diethyl ether / 1.5 h / 0 °C

2.1: 4 Angstroem molecular sieves / (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst / 12 h / 20 °C

2.2: 80 percent / conc. HCl / CHCl₃ / 4 h

3.1: 93 percent / NaBH₄ / methanol / 1 h / 20 °C

4.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

5.1: 88 percent / 10-camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; triethylamine; (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst; In methanol; diethyl ether; dichloromethane; 2.1: hetero-Diels-Alder reaction;
DOI:10.1016/S0040-4020(03)00814-7