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

Base Information

• Chemical Name: 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
• CAS No.: 190779-73-8
• Molecular Formula: C₄₀H₅₂O₁₁SSi
• Molecular Weight: 768.998

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 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

There total 3 articles about 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 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:

ethyl-3,4,6-tri-O-acetyl-2-O-benzyl-1-thio-D-glucopyranoside (190779-52-3) → 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)

Guidance literature:

Multi-step reaction with 4 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

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

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 2,6-dimethylpyridine; dmap; dibenzoyl peroxide; In pyridine; 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-bis-(4-methoxy-benzyloxy)-propoxy]-tetrahydro-pyran-4-yl ester (190779-66-9) → 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)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / CAN / acetonitrile; H₂O / 0.5 h / Ambient temperature

2: 62 percent / DMAP / pyridine / 48 h / 60 °C

3: 63 percent / 2,6-lutidine, BPO / acetonitrile / 0.5 h / Ambient temperature

With 2,6-dimethylpyridine; dmap; ammonium cerium(IV) nitrate; dibenzoyl peroxide; In pyridine; water; acetonitrile;

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

upstream raw materials:

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

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

Downstream raw materials:

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

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

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-{(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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