(2R,3R,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol

Base Information

Chemical Name:(2R,3R,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol
CAS No.:842141-76-8
Molecular Formula:C₃₃H₅₂O₆Si
Molecular Weight:572.858
Hs Code.:

Synonyms:

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Chemical Property of (2R,3R,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol

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Technology Process of (2R,3R,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol

There total 12 articles about (2R,3R,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol 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:

: 756834-72-7
(3S,4S)-3-methyl-6-<(tert-butyldimethylsilyl)oxy>-1-hexen-4-ol

: 842141-76-8
(2R,3R,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 13 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂

2: 48 percent / OsO₄; aq. NMO / tetrahydrofuran

3: 81 percent / p-TsOH; CuSO₄ / 20 °C

4: 80 percent / TPAP; NMO; molecular sieves / CH₂Cl₂

5: 92 percent / 18-crown-6; KHMDS / tetrahydrofuran / -78 °C

6: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

7: 67 percent / D-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves

8: 80 percent / NaH; Bu₄NI

9: 52 percent / CSA / CH₂Cl₂; propan-2-ol

10: 91 percent / imidazole / dimethylformamide

11: 71 percent / NaH; Bu₄NI

12: 83 percent / TBAF / tetrahydrofuran

13: 91 percent / imidazole / dimethylformamide

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; 18-crown-6 ether; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; 5: Horner-Wadsworth-Emmons reaction;
DOI:10.1055/s-2004-835661

Reference yield:

: 842141-55-3
(3S,4S)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-triisopropylsilanyloxy-pentanal

: 842141-76-8
(2R,3R,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 92 percent / 18-crown-6; KHMDS / tetrahydrofuran / -78 °C

2: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3: 67 percent / D-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves

4: 80 percent / NaH; Bu₄NI

5: 52 percent / CSA / CH₂Cl₂; propan-2-ol

6: 91 percent / imidazole / dimethylformamide

7: 71 percent / NaH; Bu₄NI

8: 83 percent / TBAF / tetrahydrofuran

9: 91 percent / imidazole / dimethylformamide

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; 1: Horner-Wadsworth-Emmons reaction;
DOI:10.1055/s-2004-835661

Reference yield:

: 842141-72-4
(3S,4S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-4-triisopropylsilanyloxy-hex-1-ene

: 842141-76-8
(2R,3R,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 48 percent / OsO₄; aq. NMO / tetrahydrofuran

2: 81 percent / p-TsOH; CuSO₄ / 20 °C

3: 80 percent / TPAP; NMO; molecular sieves / CH₂Cl₂

4: 92 percent / 18-crown-6; KHMDS / tetrahydrofuran / -78 °C

5: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 67 percent / D-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves

7: 80 percent / NaH; Bu₄NI

8: 52 percent / CSA / CH₂Cl₂; propan-2-ol

9: 91 percent / imidazole / dimethylformamide

10: 71 percent / NaH; Bu₄NI

11: 83 percent / TBAF / tetrahydrofuran

12: 91 percent / imidazole / dimethylformamide

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; 18-crown-6 ether; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; 4: Horner-Wadsworth-Emmons reaction;
DOI:10.1055/s-2004-835661