3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one

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Chemical Name:3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one
CAS No.:362624-15-5
Molecular Formula:C₃₉H₅₆O₁₀
Molecular Weight:684.868
Hs Code.:

Synonyms:3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one

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Chemical Property of 3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one

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Technology Process of 3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one

There total 35 articles about 3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one 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: 67.0%

: 362624-14-4
(E)-2-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-6-{2-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxymethoxy-propyl]-[1,3]dioxolan-2-yl}-2-methyl-hex-4-en-3-one

: 362624-15-5
3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/S0040-4039(01)00841-3

Reference yield:

: 5694-95-1
2-(2-(2-hydroxyethyl)-1,3-dioxolan-2-yl)ethanol

: 362624-15-5
3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one

Guidance literature:: Multi-step reaction with 16 steps

1: 75 percent / NaH / tetrahydrofuran / 0 °C

2: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

3: CH₂Cl₂

4: 85 percent / DIBAL-H / CH₂Cl₂ / -78 °C

5: 82 percent / D(-)DIPT; TBHP / Ti(O-i-Pr)4 / CH₂Cl₂ / 9 h / -20 °C

6: 90 percent / TPP; I₂; imidazole / diethyl ether; acetonitrile / 20 °C

7: 95 percent / Zn; NaI / methanol / Heating

8: 97 percent / imidazole / dimethylformamide / 20 °C

9: 90 percent / OsO₄; NMO / acetone; H₂O / 20 °C

10: 87 percent / NaIO₄ / tetrahydrofuran; H₂O / 20 °C

11: 80 percent / NaBH₄ / methanol / 0 °C

12: 95 percent / (i-Pr)2NEt / CH₂Cl₂ / 20 °C

13: 96 percent / Pd/C / ethyl acetate / 20 °C

14: 85 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

15: 60 percent / LDA / -78 - 20 °C

16: 67 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; iodine; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; lithium diisopropyl amide; titanium(IV) isopropylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 2: Swern oxidation / 3: Wittig olefination / 5: Sharpless asymmetric epoxidation / 14: Swern oxidation / 15: Horner-Wadsworth-Emmons coupling;
DOI:10.1016/S0040-4039(01)00841-3

Reference yield:

: 6506-31-6
dimethyl acetonedicarboxylate ethylene ketal

: 362624-15-5
3-[(4S,6R)-6-((S)-2,4-Bis-benzyloxy-butyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-1-((7R,9R)-9-methoxymethoxymethyl-1,4,8-trioxa-spiro[4.5]dec-7-yl)-3-methyl-butan-2-one

Guidance literature:: Multi-step reaction with 17 steps

1: 80 percent / LiAlH₄ / tetrahydrofuran / Heating

2: 75 percent / NaH / tetrahydrofuran / 0 °C

3: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 - 0 °C

4: CH₂Cl₂

5: 85 percent / DIBAL-H / CH₂Cl₂ / -78 °C

6: 82 percent / D(-)DIPT; TBHP / Ti(O-i-Pr)4 / CH₂Cl₂ / 9 h / -20 °C

7: 90 percent / TPP; I₂; imidazole / diethyl ether; acetonitrile / 20 °C

8: 95 percent / Zn; NaI / methanol / Heating

9: 97 percent / imidazole / dimethylformamide / 20 °C

10: 90 percent / OsO₄; NMO / acetone; H₂O / 20 °C

11: 87 percent / NaIO₄ / tetrahydrofuran; H₂O / 20 °C

12: 80 percent / NaBH₄ / methanol / 0 °C

13: 95 percent / (i-Pr)2NEt / CH₂Cl₂ / 20 °C

14: 96 percent / Pd/C / ethyl acetate / 20 °C

15: 85 percent / (COCl)2; Et₃N; DMSO / CH₂Cl₂ / -78 °C

16: 60 percent / LDA / -78 - 20 °C

17: 67 percent / TBAF / tetrahydrofuran / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; iodine; thiamine diphosphate; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; lithium diisopropyl amide; titanium(IV) isopropylate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 3: Swern oxidation / 4: Wittig olefination / 6: Sharpless asymmetric epoxidation / 15: Swern oxidation / 16: Horner-Wadsworth-Emmons coupling;
DOI:10.1016/S0040-4039(01)00841-3