(2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol

Base Information

Chemical Name:(2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol
CAS No.:618096-72-3
Molecular Formula:C₃₉H₇₄O₇Si₂
Molecular Weight:711.183
Hs Code.:

(2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol

Synonyms:(2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol

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Chemical Property of (2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol

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Technology Process of (2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol

There total 15 articles about (2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol 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: 86.0%

: (S)-8-(tert-Butyl-dimethyl-silanyloxy)-4-hydroxy-1-{(2S,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octan-2-one

: 618096-72-3
(2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol

Guidance literature:: With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -35 - -15 ℃; for 30h;
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

: 618096-72-3
(2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol

Guidance literature:: Multi-step reaction with 10 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: NaBH₄ / methanol / 1 h / 20 °C

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

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

5.1: pyridine / CH₂Cl₂ / 1 h / -10 °C

6.1: LDA; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C

6.2: tetrahydrofuran; hexane / -78 - 20 °C

7.1: K₂CO₃ / methanol / 12 h / 20 °C

8.1: 86 percent / pyridinium p-toluenesulfonate; Hg(OAc)2; H₂O / tetrahydrofuran / 1.5 h / 45 °C

9.1: Et₃N; c-Hex₂BCl / diethyl ether / 0.5 h / 0 °C

9.2: 86 percent / diethyl ether / 20 h / -78 - -30 °C

10.1: 86 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 30 h / -35 - -15 °C

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; dicyclohexylboron chloride; mercury(II) diacetate; water; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetic acid; acetonitrile; 1.1: hetero-Diels-Alder reaction / 10.1: Evans-Saksena reduction;
DOI:10.1016/S0040-4020(03)00814-7

Reference yield:

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

: 618096-72-3
(2R,4R,5S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-{(2R,4S,6S)-6-[2-(4-methoxy-benzyloxy)-ethyl]-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl}-5-methyl-octane-2,4-diol

Guidance literature:: Multi-step reaction with 11 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: NaBH₄ / methanol / 1 h / 20 °C

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

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

6.1: pyridine / CH₂Cl₂ / 1 h / -10 °C

7.1: LDA; HMPA / tetrahydrofuran; hexane / 0.25 h / -78 °C

7.2: tetrahydrofuran; hexane / -78 - 20 °C

8.1: K₂CO₃ / methanol / 12 h / 20 °C

9.1: 86 percent / pyridinium p-toluenesulfonate; Hg(OAc)2; H₂O / tetrahydrofuran / 1.5 h / 45 °C

10.1: Et₃N; c-Hex₂BCl / diethyl ether / 0.5 h / 0 °C

10.2: 86 percent / diethyl ether / 20 h / -78 - -30 °C

11.1: 86 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 30 h / -35 - -15 °C

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 4 A molecular sieve; (1S)-10-camphorsulfonic acid; dicyclohexylboron chloride; mercury(II) diacetate; water; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; (1S,2R)-1-amino-2-indanol-derived tridentate Cr catalyst; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetic acid; acetonitrile; 2.1: hetero-Diels-Alder reaction / 11.1: Evans-Saksena reduction;
DOI:10.1016/S0040-4020(03)00814-7