(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-8,8-dimethoxy-3,5-dimethyl-6-triisopropylsilanyloxy-octanoic acid benzyl ester

Base Information

Chemical Name:(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-8,8-dimethoxy-3,5-dimethyl-6-triisopropylsilanyloxy-octanoic acid benzyl ester
CAS No.:198757-94-7
Molecular Formula:C₃₇H₅₈O₈Si
Molecular Weight:658.948
Hs Code.:

Synonyms:(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-8,8-dimethoxy-3,5-dimethyl-6-triisopropylsilanyloxy-octanoic acid benzyl ester

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Chemical Property of (3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-8,8-dimethoxy-3,5-dimethyl-6-triisopropylsilanyloxy-octanoic acid benzyl ester

Chemical Property:

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Technology Process of (3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-8,8-dimethoxy-3,5-dimethyl-6-triisopropylsilanyloxy-octanoic acid benzyl ester

There total 1 articles about (3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-8,8-dimethoxy-3,5-dimethyl-6-triisopropylsilanyloxy-octanoic acid benzyl ester 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:

: 67-56-1
methanol

: 161926-48-3
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester

: 198757-94-7
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-8,8-dimethoxy-3,5-dimethyl-6-triisopropylsilanyloxy-octanoic acid benzyl ester

Guidance literature:: With toluene-4-sulfonic acid; Yield given;
DOI:10.1021/ja9743194

Reference yield:

: 198757-94-7
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-8,8-dimethoxy-3,5-dimethyl-6-triisopropylsilanyloxy-octanoic acid benzyl ester

: 198758-11-1
(R)-N-{3-[(Z)-(5R,6S,7S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,9-dimethoxy-4,6-dimethyl-7-triisopropylsilanyloxy-non-3-enyl]-2,5-dimethoxy-phenyl}-4-hydroxy-3-methoxy-butyramide

Guidance literature:: Multi-step reaction with 9 steps

1.1: 98 percent / H₂ / Pd/C

2.1: 95 percent / DBU / tetrahydrofuran

3.1: 70 percent / LAH; TMEDA

4.1: 92 percent

5.1: 85 percent / HF*Pyr

6.1: 82 percent / Me(PhO)3PI

7.1: LHMDS / tetrahydrofuran / -78 °C

7.2: 80 percent / tetrahydrofuran

8.1: 98 percent / Na(Hg); Na₂HPO₄

9.1: 95 percent / HF*Pyr / pyridine

With disodium hydrogenphosphate; lithium aluminium tetrahydride; sodium amalgam; N,N,N,N,-tetramethylethylenediamine; methyltriphenoxyphosphonium iodide; hydrogen; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; 1.1: Hydrogenolysis / 2.1: Elimination / 3.1: Reduction / 4.1: silylation / 5.1: desilylation / 6.1: Iodination / 7.1: Metallation / 7.2: Alkylation / 8.1: Reduction / 9.1: desilylation;
DOI:10.1021/jo971793j

Reference yield:

: 198757-94-7
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-8,8-dimethoxy-3,5-dimethyl-6-triisopropylsilanyloxy-octanoic acid benzyl ester

: (R)-2-(Cyclohexanecarbonyl-amino)-propionic acid (6E,8E,10E,16Z)-(5R,13S,14S,15R)-15-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-14,16-dimethyl-3,22,24-trioxo-2-aza-bicyclo[18.3.1]tetracosa-1⁽²³⁾,6,8,10,16,20-hexaen-13-yl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: 98 percent / H₂ / Pd/C

2.1: 95 percent / DBU / tetrahydrofuran

3.1: 70 percent / LAH; TMEDA

4.1: 92 percent

5.1: 85 percent / HF*Pyr

6.1: 82 percent / Me(PhO)3PI

7.1: LHMDS / tetrahydrofuran / -78 °C

7.2: 80 percent / tetrahydrofuran

8.1: 98 percent / Na(Hg); Na₂HPO₄

9.1: 95 percent / HF*Pyr / pyridine

10.1: 80 percent / Pyr*SO₃ / dimethylsulfoxide

11.1: 90 percent / PPTS / acetone

12.1: 70 percent / CrCl₂

13.1: Pd(MeCN)2Cl₂ / dimethylformamide; tetrahydrofuran

14.1: pTsOH / methanol

15.1: DMAP / CH₂Cl₂ / -78 °C

16.1: Et₂NH / CH₂Cl₂

17.1: BOP; Et₃N / CH₂Cl₂

18.1: CAN / tetrahydrofuran; H₂O

With chromium dichloride; dmap; disodium hydrogenphosphate; lithium aluminium tetrahydride; sodium amalgam; ammonium cerium(IV) nitrate; N,N,N,N,-tetramethylethylenediamine; methyltriphenoxyphosphonium iodide; hydrogen; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; diethylamine; triethylamine; lithium hexamethyldisilazane; dichloro bis(acetonitrile) palladium(II); palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 1.1: Hydrogenolysis / 2.1: Elimination / 3.1: Reduction / 4.1: silylation / 5.1: desilylation / 6.1: Iodination / 7.1: Metallation / 7.2: Alkylation / 8.1: Reduction / 9.1: desilylation / 10.1: Parikh-Doering oxidation / 11.1: Hydrolysis / 12.1: Condensation / 13.1: Cyclization / 14.1: desilylation / 15.1: Esterification / 16.1: deacylation / 17.1: Acylation / 18.1: Oxidation;
DOI:10.1021/jo971793j