Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-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-hydroxy-propoxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 190779-71-6
• Molecular Formula: C₃₈H₄₈O₁₁Si
• Molecular Weight: 708.878

Synonyms:Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-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-hydroxy-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-hydroxy-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-hydroxy-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: 62.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 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-hydroxy-propoxy]-tetrahydro-pyran-4-yl ester (190779-71-6)

Guidance literature:

With dmap; In pyridine; at 60 ℃; for 48h;

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 (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-propoxy]-tetrahydro-pyran-4-yl ester (190779-71-6)

Guidance literature:

Multi-step reaction with 3 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

With dmap; N-iodo-succinimide; ammonium cerium(IV) nitrate; trifluorormethanesulfonic acid; 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-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-hydroxy-propoxy]-tetrahydro-pyran-4-yl ester (190779-71-6)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; ammonium cerium(IV) nitrate; In pyridine; water; acetonitrile;

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

upstream raw materials:

tert-butylchlorodiphenylsilane

Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-((R)-2,3-dihydroxy-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-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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