(3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexan-1-ol

Base Information

• Chemical Name: (3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexan-1-ol
• CAS No.: 852245-25-1
• Molecular Formula: C₂₉H₅₂O₇Si
• Molecular Weight: 540.813

Synonyms:(3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexan-1-ol

Chemical Property of (3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexan-1-ol

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Technology Process of (3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexan-1-ol

There total 24 articles about (3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexan-1-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: 65.0%

tert-Butyl-{(2R,5R)-5-[(1R,4S)-1-(4-methoxy-benzyloxy)-4-methoxymethoxy-4-methyl-hex-5-enyl]-2-methyl-tetrahydro-furan-2-ylmethoxy}-dimethyl-silane (852245-11-5) → (3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexan-1-ol (852245-25-1)

Guidance literature:

tert-Butyl-{(2R,5R)-5-[(1R,4S)-1-(4-methoxy-benzyloxy)-4-methoxymethoxy-4-methyl-hex-5-enyl]-2-methyl-tetrahydro-furan-2-ylmethoxy}-dimethyl-silane; With borane-THF; In tetrahydrofuran; at 20 ℃; for 2h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 24h;

DOI:10.1021/ol0504291

Reference yield:

(S)-5-Benzyloxy-2-methyl-pentane-1,2-diol (852245-21-7) → (3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexan-1-ol (852245-25-1)

Guidance literature:

Multi-step reaction with 19 steps

1.1: Et₃N; DMAP / CH₂Cl₂ / 72 h / 20 °C

2.1: (i-Pr)2NEt / CH₂Cl₂ / 72 h / 20 °C

3.1: 12.45 g / H₂ / Pd/C / ethanol / 48 h

4.1: 80 percent / Ph₃P; DIAD / tetrahydrofuran / 20 °C

5.1: mCPBA; NaHCO₃ / CH₂Cl₂ / 17 h

6.1: 85 percent / potassium hexamethyldisilazide / 1,2-dimethoxy-ethane; toluene / -70 - 0 °C

7.1: 95 percent / TBAF / tetrahydrofuran

8.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h

9.1: 2-methyl-2-butene; NaClO₂; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; H₂O / 20 °C

10.1: 80 mg / diethyl ether

11.1: acetic acid / H₂O / 5 h / 0 °C

12.1: 0.220 g / Et₃N / CH₂Cl₂

13.1: 99 percent / DBU / CH₂Cl₂ / 3 h / 20 °C

14.1: AD-mix-β / H2O; 2-methyl-propan-2-ol / 6 h / 0 °C

14.2: 78 percent / H₂S / 2-methyl-propan-2-ol; H₂O

15.1: 72 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

16.1: Dibal-H / CH₂Cl₂; toluene / 6 h / -78 °C

17.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / 0 °C

17.2: 190 mg / tetrahydrofuran; toluene / 1 h / 20 °C

18.1: 64 percent / KH / tetrahydrofuran / 20 °C

19.1: BH₃*THF / tetrahydrofuran / 2 h / 20 °C

19.2: 65 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O; methanol / 24 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; borane-THF; 2-methyl-but-2-ene; di-isopropyl azodicarboxylate; AD-mix-β; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; toluene; tert-butyl alcohol; 4.1: Mitsunobu reaction / 6.1: Julia-Lythgoe coupling / 14.1: Sharpless dihydroxylation / 17.2: Wittig olefination;

DOI:10.1021/ol0504291

Reference yield:

4-methyl-4-penten-1-ol (22508-64-1) → (3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexan-1-ol (852245-25-1)

Guidance literature:

Multi-step reaction with 21 steps

1.1: NaH / dimethylformamide / 12 h

2.1: (DHQ)2PHAL; K₃Fe(CN)6; K₂CO₃ / K₂OsO₂(OH)4 / H₂O; 2-methyl-propan-2-ol / 7 h

3.1: Et₃N; DMAP / CH₂Cl₂ / 72 h / 20 °C

4.1: (i-Pr)2NEt / CH₂Cl₂ / 72 h / 20 °C

5.1: 12.45 g / H₂ / Pd/C / ethanol / 48 h

6.1: 80 percent / Ph₃P; DIAD / tetrahydrofuran / 20 °C

7.1: mCPBA; NaHCO₃ / CH₂Cl₂ / 17 h

8.1: 85 percent / potassium hexamethyldisilazide / 1,2-dimethoxy-ethane; toluene / -70 - 0 °C

9.1: 95 percent / TBAF / tetrahydrofuran

10.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h

11.1: 2-methyl-2-butene; NaClO₂; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; H₂O / 20 °C

12.1: 80 mg / diethyl ether

13.1: acetic acid / H₂O / 5 h / 0 °C

14.1: 0.220 g / Et₃N / CH₂Cl₂

15.1: 99 percent / DBU / CH₂Cl₂ / 3 h / 20 °C

16.1: AD-mix-β / H2O; 2-methyl-propan-2-ol / 6 h / 0 °C

16.2: 78 percent / H₂S / 2-methyl-propan-2-ol; H₂O

17.1: 72 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

18.1: Dibal-H / CH₂Cl₂; toluene / 6 h / -78 °C

19.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h / 0 °C

19.2: 190 mg / tetrahydrofuran; toluene / 1 h / 20 °C

20.1: 64 percent / KH / tetrahydrofuran / 20 °C

21.1: BH₃*THF / tetrahydrofuran / 2 h / 20 °C

21.2: 65 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O; methanol / 24 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; borane-THF; Hydroquinone 1,4-phthalazinediyl diether; 2-methyl-but-2-ene; di-isopropyl azodicarboxylate; AD-mix-β; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hexacyanoferrate(III); palladium on activated charcoal; potassium dioxotetrahydroxoosmate(VI); In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.1: Sharpless dihydroxylation / 6.1: Mitsunobu reaction / 8.1: Julia-Lythgoe coupling / 16.1: Sharpless dihydroxylation / 19.2: Wittig olefination;

DOI:10.1021/ol0504291

upstream raw materials:

tert-Butyl-{(2R,5R)-5-[(1R,4S)-1-(4-methoxy-benzyloxy)-4-methoxymethoxy-4-methyl-hex-5-enyl]-2-methyl-tetrahydro-furan-2-ylmethoxy}-dimethyl-silane

(S)-5-Benzyloxy-2-methyl-pentane-1,2-diol

(S)-4-(3-Benzyloxy-propyl)-2,2,4-trimethyl-[1,3]dioxolane

5-(tert-butyl-dimethyl-silanyloxy)-4-methoxymethoxy-4-methyl-pentan-1-ol

Downstream raw materials:

5-[(3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexylsulfanyl]-1-phenyl-1H-tetrazole

5-[(3S,6R)-6-[(2R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5-methyl-tetrahydro-furan-2-yl]-6-(4-methoxy-benzyloxy)-3-methoxymethoxy-3-methyl-hexane-1-sulfonyl]-1-phenyl-1H-tetrazole

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