Acetic acid (R)-1-[(3aR,5R,6S,6aS)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester

Base Information

• Chemical Name: Acetic acid (R)-1-[(3aR,5R,6S,6aS)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester
• CAS No.: 175652-63-8
• Molecular Formula: C₃₂H₄₂O₁₇S₂
• Molecular Weight: 762.807

Synonyms:

Chemical Property of Acetic acid (R)-1-[(3aR,5R,6S,6aS)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester

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Technology Process of Acetic acid (R)-1-[(3aR,5R,6S,6aS)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester

There total 5 articles about Acetic acid (R)-1-[(3aR,5R,6S,6aS)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl 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:

1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose (55951-90-1) → Acetic acid (R)-1-[(3aR,5R,6S,6aS)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester (175652-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH, 2.) 1,7,10-trioxa-4,13-diazacyclopentadecane / 1.) THF, 0 deg C, 2.) THF, RT, 2 h

2: 91 percent / 50percent aq. AcOH / 1.5 h / 60 °C

3: pyridine / 1.) - 10 deg C, 2 h, 2.) RT, 18 h

4: pyridine / 2 h

With pyridine; sodium hydride; acetic acid; Kryptofix 21;

DOI:10.1016/0008-6215(95)00339-8

Reference yield:

tetraacetyl thioglucose (19879-84-6) → Acetic acid (R)-1-[(3aR,5R,6S,6aS)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester (175652-63-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH, 2.) 1,7,10-trioxa-4,13-diazacyclopentadecane / 1.) THF, 0 deg C, 2.) THF, RT, 2 h

2: 91 percent / 50percent aq. AcOH / 1.5 h / 60 °C

3: pyridine / 1.) - 10 deg C, 2 h, 2.) RT, 18 h

4: pyridine / 2 h

With pyridine; sodium hydride; acetic acid; Kryptofix 21;

DOI:10.1016/0008-6215(95)00339-8

Reference yield:

1,2-O-isopropylidene-3-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-thio-α-D-glucofuranose (175652-62-7) → Acetic acid (R)-1-[(3aR,5R,6S,6aS)-2,2-dimethyl-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester (175652-63-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 1.) - 10 deg C, 2 h, 2.) RT, 18 h

2: pyridine / 2 h

With pyridine;

DOI:10.1016/0008-6215(95)00339-8

upstream raw materials:

acetic anhydride

tetraacetyl thioglucose

1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose

1,2-O-isopropylidene-3-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-thio-α-D-glucofuranose

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