Acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-ethoxymethyl ester

Base Information

• Chemical Name: Acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-ethoxymethyl ester
• CAS No.: 190779-75-0
• Molecular Formula: C₄₁H₅₂O₁₃Si
• Molecular Weight: 780.942

Synonyms:Acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-ethoxymethyl ester

Chemical Property of Acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-ethoxymethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-ethoxymethyl ester

There total 5 articles about Acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-ethoxymethyl 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: 85.0%

acetic acid (64-19-7,77671-22-8) + Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylsulfanylmethoxy-propoxy]-tetrahydro-pyran-4-yl ester (190779-73-8) → Acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-ethoxymethyl ester (190779-75-0)

Guidance literature:

With N-iodo-succinimide; In tetrahydrofuran; 1,2-dichloro-ethane; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0040-4020(97)00309-8

Reference yield:

ethyl-3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-D-glucopyranoside (190779-52-3) → Acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-ethoxymethyl ester (190779-75-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / NIS, TfOH / diethyl ether / 2 h / Ambient temperature

2: 87 percent / CAN / acetonitrile; H₂O / 0.5 h / Ambient temperature

3: 62 percent / DMAP / pyridine / 48 h / 60 °C

4: 63 percent / 2,6-lutidine, BPO / acetonitrile / 0.5 h / Ambient temperature

5: 85 percent / NIS / 1,2-dichloro-ethane; tetrahydrofuran / 0.08 h / 0 °C

With 2,6-dimethylpyridine; dmap; N-iodo-succinimide; ammonium cerium(IV) nitrate; trifluorormethanesulfonic acid; dibenzoyl peroxide; In tetrahydrofuran; pyridine; diethyl ether; water; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4020(97)00309-8

Reference yield:

Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((R)-2,3-dihydroxy-propoxy)-tetrahydro-pyran-4-yl ester (190779-69-2) → Acetic acid (S)-2-(tert-butyl-diphenyl-silanyloxy)-1-((2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-ethoxymethyl ester (190779-75-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 62 percent / DMAP / pyridine / 48 h / 60 °C

2: 63 percent / 2,6-lutidine, BPO / acetonitrile / 0.5 h / Ambient temperature

3: 85 percent / NIS / 1,2-dichloro-ethane; tetrahydrofuran / 0.08 h / 0 °C

With 2,6-dimethylpyridine; dmap; N-iodo-succinimide; dibenzoyl peroxide; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4020(97)00309-8

upstream raw materials:

acetic acid

Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methylsulfanylmethoxy-propoxy]-tetrahydro-pyran-4-yl ester

ethyl-3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-D-glucopyranoside

Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((R)-2,3-dihydroxy-propoxy)-tetrahydro-pyran-4-yl ester

Downstream raw materials:

Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-6-[(S)-2-(6-benzoylamino-purin-9-ylmethoxy)-3-(tert-butyl-diphenyl-silanyloxy)-propoxy]-5-benzyloxy-tetrahydro-pyran-4-yl ester

N-{9-[(S)-1-((2S,3R,4S,5S,6R)-3-Benzyloxy-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxymethyl)-2-(tert-butyl-diphenyl-silanyloxy)-ethoxymethyl]-9H-purin-6-yl}-benzamide

N-(9-{(R)-2-{(2S,3R,4S,5S,6R)-3-Benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4,5-dihydroxy-tetrahydro-pyran-2-yloxy}-1-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-ethoxymethyl}-9H-purin-6-yl)-benzamide

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