((2S,4S)-4-Azido-1-oxo-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: ((2S,4S)-4-Azido-1-oxo-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane
• CAS No.: 478158-95-1
• Molecular Formula: C₂₁H₂₇N₃O₂SSi
• Molecular Weight: 413.616

Synonyms:((2S,4S)-4-Azido-1-oxo-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane

Chemical Property of ((2S,4S)-4-Azido-1-oxo-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane

Chemical Property:

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Technology Process of ((2S,4S)-4-Azido-1-oxo-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane

There total 4 articles about ((2S,4S)-4-Azido-1-oxo-tetrahydro-1λ⁴-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane 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: 95.0%

((2S,4S)-4-Azido-tetrahydro-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane (478158-94-0) → ((2S,4S)-4-Azido-1-oxo-tetrahydro-1λ4-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane (478158-95-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1016/S0960-894X(02)00394-3

Reference yield:

(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol (478158-91-7) → ((2S,4S)-4-Azido-1-oxo-tetrahydro-1λ4-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane (478158-95-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / PPh₃; DEAD / tetrahydrofuran / 15 h / 50 °C

2: 65 percent / NH₃ / methanol / 15 h / 20 °C

3: 87 percent / PPh₃; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 1 h / 0 °C

4: 95 percent / mCPBA / CH₂Cl₂ / 2 h / -78 °C

With diphenylphosphoranyl azide; ammonia; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 1: Mitsunobu reaction / 3: Mitsunobu reaction;

DOI:10.1016/S0960-894X(02)00394-3

Reference yield:

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol (478158-93-9) → ((2S,4S)-4-Azido-1-oxo-tetrahydro-1λ4-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane (478158-95-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / PPh₃; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 1 h / 0 °C

2: 95 percent / mCPBA / CH₂Cl₂ / 2 h / -78 °C

With diphenylphosphoranyl azide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1: Mitsunobu reaction;

DOI:10.1016/S0960-894X(02)00394-3

upstream raw materials:

((2S,4S)-4-Azido-tetrahydro-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane

(3S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol

(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-ol

Benzoic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester

Downstream raw materials:

Acetic acid (3S,5S)-3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl ester

9-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-6-chloro-9H-purine

N-{1-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

N-{1-[3-azido-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

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