(Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal

Base Information

• Chemical Name: (Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal
• CAS No.: 228252-17-3
• Molecular Formula: C₂₇H₅₆O₄Si₂
• Molecular Weight: 500.91
• Mol file: 228252-17-3.mol

Synonyms:(Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal

Chemical Property of (Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal

There total 1 articles about (Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal 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:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal (228252-17-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to room temperature, 30 min

2: 96 percent / DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(99)00128-3

Reference yield:

(Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal (228252-17-3) → (3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene (306769-38-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: CrCl₂ / dioxane; tetrahydrofuran / 0.5 h / 22 °C

2.1: 268 mg / APTS / methanol / 0.5 h / 22 °C

3.1: 74 percent / (MeCN)2PdCl₂ / dimethylformamide / 2 h / 22 °C

4.1: 92 percent / (Cl₃C)2CO; PPh₃ / tetrahydrofuran / 0.67 h / 22 °C

5.1: 749 mg / Cs₂CO₃; CsI / acetone / 15 h / 60 °C

6.1: 72 percent / LiI*2H₂O; 2,4,6-collidine / 15 h / 100 °C

7.1: NaI; 15-crown-5 ether / CH₂Cl₂ / 0.08 h / 22 °C

7.2: bromomethylborane / CH₂Cl₂; diethyl ether / -78 - 22 °C

7.3: dimethylformamide; CH₂Cl₂; diethyl ether / 6 h / 55 °C

8.1: 330 mg / K₂CO₃ / methanol / 15 h / 22 °C

9.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 22 °C

10.1: 81 percent / Et₃N / toluene / 30 h / 220 °C

11.1: KHMDS / tetrahydrofuran; toluene / 0.58 h / -78 - 0 °C

11.2: 95 percent / tetrahydrofuran; toluene / 2.08 h / -78 - 0 °C

12.1: m-CPBA; Li₂CO₃ / CH₂Cl₂ / 3 h / -78 °C

13.1: APTS / CH₂Cl₂ / 2.75 h / 0 °C

13.2: 3.9 mg / sodium borohydride / ethanol / 3 h / 0 °C

14.1: NaH; n-Bu₄NI / tetrahydrofuran; dimethylformamide / 6 h / 22 °C

With 2,4,6-trimethyl-pyridine; chromium dichloride; isocyanate de chlorosulfonyle; 15-crown-5; 1,1,1,3,3,3-hexachloro-propan-2-one; tetra-(n-butyl)ammonium iodide; lithium carbonate; potassium hexamethylsilazane; sodium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; sodium iodide; lithium iodide; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Takai homologation / 2.1: Desilylation / 3.1: Stille coupling / 4.1: Substitution / 5.1: Cyclization / 6.1: Decarboxylation / 7.1: Substitution / 7.2: Substitution / 7.3: Acetoxylation / 8.1: Deacetylation / 9.1: Dess-Martin oxidation / 10.1: Tandem transannular Diels-Alder-aldol reaction / 11.1: Wittig reaction / 11.2: Wittig reaction / 12.1: Epoxidation / 13.1: Addition / 13.2: Reduction / 14.1: Benzylation;

DOI:10.1021/jo0007635

Reference yield:

(Z)-(2R,3S)-8-(tert-butyldimethylsilyl)oxy-7-methoxymethyl-2,6-dimethyl-3-(triisopropylsilyl)oxy-6-octenal (228252-17-3) → (4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-noraphidicol-6-en-3-one

Guidance literature:

Multi-step reaction with 16 steps

1.1: CrCl₂ / dioxane; tetrahydrofuran / 0.5 h / 22 °C

2.1: 268 mg / APTS / methanol / 0.5 h / 22 °C

3.1: 74 percent / (MeCN)2PdCl₂ / dimethylformamide / 2 h / 22 °C

4.1: 92 percent / (Cl₃C)2CO; PPh₃ / tetrahydrofuran / 0.67 h / 22 °C

5.1: 749 mg / Cs₂CO₃; CsI / acetone / 15 h / 60 °C

6.1: 72 percent / LiI*2H₂O; 2,4,6-collidine / 15 h / 100 °C

7.1: NaI; 15-crown-5 ether / CH₂Cl₂ / 0.08 h / 22 °C

7.2: bromomethylborane / CH₂Cl₂; diethyl ether / -78 - 22 °C

7.3: dimethylformamide; CH₂Cl₂; diethyl ether / 6 h / 55 °C

8.1: 330 mg / K₂CO₃ / methanol / 15 h / 22 °C

9.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 22 °C

10.1: 81 percent / Et₃N / toluene / 30 h / 220 °C

11.1: KHMDS / tetrahydrofuran; toluene / 0.58 h / -78 - 0 °C

11.2: 95 percent / tetrahydrofuran; toluene / 2.08 h / -78 - 0 °C

12.1: m-CPBA; Li₂CO₃ / CH₂Cl₂ / 3 h / -78 °C

13.1: APTS / CH₂Cl₂ / 2.75 h / 0 °C

13.2: 3.9 mg / sodium borohydride / ethanol / 3 h / 0 °C

14.1: NaH; n-Bu₄NI / tetrahydrofuran; dimethylformamide / 6 h / 22 °C

15.1: 3.0 mg / TBAF / tetrahydrofuran / 15 h / 22 °C

16.1: 71 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 22 °C

With 2,4,6-trimethyl-pyridine; chromium dichloride; isocyanate de chlorosulfonyle; 15-crown-5; 1,1,1,3,3,3-hexachloro-propan-2-one; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; lithium carbonate; potassium hexamethylsilazane; sodium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 8-aminopyrene-1,3,6-trisulfonic acid, trisodium salt; sodium iodide; lithium iodide; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Takai homologation / 2.1: Desilylation / 3.1: Stille coupling / 4.1: Substitution / 5.1: Cyclization / 6.1: Decarboxylation / 7.1: Substitution / 7.2: Substitution / 7.3: Acetoxylation / 8.1: Deacetylation / 9.1: Dess-Martin oxidation / 10.1: Tandem transannular Diels-Alder-aldol reaction / 11.1: Wittig reaction / 11.2: Wittig reaction / 12.1: Epoxidation / 13.1: Addition / 13.2: Reduction / 14.1: Benzylation / 15.1: Desilylation / 16.1: Dess-Martin oxidation;

DOI:10.1021/jo0007635

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

Downstream raw materials:

(3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-noraphidicol-6-en-3-ol

(3S,4S,11R,16R)-17-benzyloxy-8-epi-11,16-[(S)-ethylidene]dioxy-19-nor-3-(triisopropylsilyloxy)aphidicol-6-ene