(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-formyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

Base Information

• Chemical Name: (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-formyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide
• CAS No.: 634912-02-0
• Molecular Formula: C₃₀H₄₃NO₃Si₂
• Molecular Weight: 521.847

Synonyms:(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-formyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

Chemical Property of (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-formyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-formyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

There total 5 articles about (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-formyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide 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: 94.6%

(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide (634912-00-8) → (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-formyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide (634912-02-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -65 - 5 ℃; for 0.75h;

DOI:10.1016/j.tet.2003.09.005

Reference yield:

(2S)-3-[(trimethyl-silanyl)-ethynyl]-cyclopent-2-enol (634911-85-6) → (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-formyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide (634912-02-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / xylene / 2 h / Heating

2: N-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 1.5 h / 0 - 20 °C

3: sodium periodate / tetrahydrofuran; H₂O / 1 h / 0 °C

4: 5.47 g / sodium borohydride / ethanol / 0.33 h / 20 °C

5: 75.3 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / -5 °C

6: 94.6 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 0.75 h / -65 - 5 °C

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; xylene; tert-butyl alcohol; 1: Claisen-Eschenmoser rearrangement / 6: Swern oxidation;

DOI:10.1016/j.tet.2003.09.005

Reference yield:

(2R)-N,N-dimethyl-2-[1-[(trimethyl-silanyl)-ethynyl]-cyclopent-2-enyl]-acetamide (634911-86-7) → (3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-formyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide (634912-02-0)

Guidance literature:

Multi-step reaction with 5 steps

1: N-methylmorpholine N-oxide; osmium tetroxide / acetone; H₂O; 2-methyl-propan-2-ol / 1.5 h / 0 - 20 °C

2: sodium periodate / tetrahydrofuran; H₂O / 1 h / 0 °C

3: 5.47 g / sodium borohydride / ethanol / 0.33 h / 20 °C

4: 75.3 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2.5 h / -5 °C

5: 94.6 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 0.75 h / -65 - 5 °C

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; tert-butyl alcohol; 5: Swern oxidation;

DOI:10.1016/j.tet.2003.09.005

upstream raw materials:

(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

(2S)-3-[(trimethyl-silanyl)-ethynyl]-cyclopent-2-enol

(2R)-N,N-dimethyl-2-[1-[(trimethyl-silanyl)-ethynyl]-cyclopent-2-enyl]-acetamide

(3S)-3-(3-hydroxy-propyl)-3-hydroxymethyl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

Downstream raw materials:

(3S)-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-5-trimethylsilanyl-pent-4-ynoic acid dimethylamide

(3'S)-3-(2-acetoxy-ethyl)-2-[6'-(tert-butyl-diphenyl-silanyloxy)-3'-dimethylcarbamoylmethyl-3'-[1,3]dioxolan-2''-yl-hexyl]-6,7-dimethoxy-indole-1-carboxylic acid tert-butyl ester

(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pent-4-ynoic acid dimethylamide

(3S)-5-[3-(2-acetoxy-ethyl)-6,7-dimethoxy-1H-indol-2-yl]-3-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-[1,3]dioxolan-2-yl-pentanoic acid dimethylamide

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