(4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-2-one
• CAS No.: 528864-92-8
• Molecular Formula: C₃₇H₄₉NO₅Si
• Molecular Weight: 615.885

Synonyms:(4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-2-one

Chemical Property of (4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-2-one

There total 3 articles about (4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-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: 81.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (4S,2'R,3'R)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-isopropyl-1,3-oxazolidin-2-one (528864-90-6) → (4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-2-one (528864-92-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 23h;

DOI:10.1016/S0040-4020(02)01514-4

Reference yield:

5-benzyloxy-1-pentanal (78999-24-3) → (4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-2-one (528864-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

1.2: CH₂Cl₂ / -78 - 20 °C

1.3: 88 percent / aq. H₂O₂ / methanol; CH₂Cl₂; aq. phosphate buffer / 0 - 20 °C

2.1: 81 percent / imidazole / dimethylformamide / 23 h

With 1H-imidazole; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)01514-4

Reference yield:

N-isopropyl oxazolidinone (77877-19-1,165657-81-8) → (4S,2'R,3'R)-3-[7'-benzyloxy-3'-(tert-butyldiphenylsilanyloxy)-2'-methylheptanoyl]-4-isopropyl-1,3-oxazolidin-2-one (528864-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

1.2: CH₂Cl₂ / -78 - 20 °C

1.3: 88 percent / aq. H₂O₂ / methanol; CH₂Cl₂; aq. phosphate buffer / 0 - 20 °C

2.1: 81 percent / imidazole / dimethylformamide / 23 h

With 1H-imidazole; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(02)01514-4

upstream raw materials:

tert-butylchlorodiphenylsilane

(4S,2'R,3'R)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-isopropyl-1,3-oxazolidin-2-one

5-benzyloxy-1-pentanal

N-isopropyl oxazolidinone

Downstream raw materials:

(2R,3R)-7-(benzyloxy)-3-(tert-butyldiphenylsilyloxy)-2-methylheptanol

{2-[(E)-(4R,5R)-4-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-8-phenyl-oct-7-enyl]-[1,3]dithian-2-yl}-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methanol

Acetic acid (E)-(1R,2R)-1-(3-{2-[(R)-hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-propyl)-2-methyl-5-phenyl-pent-4-enyl ester

(E)-(4R,5R)-1-{2-[(R)-Hydroxy-((4R,5R,4'S,5'R)-4,4',5'-tris-benzyloxymethyl-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-methyl]-[1,3]dithian-2-yl}-5-methyl-8-phenyl-oct-7-en-4-ol

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