2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Base Information

• Chemical Name: 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 214467-67-1
• Molecular Formula: C₅₇H₅₇NO₁₁S
• Molecular Weight: 964.146

Synonyms:

Chemical Property of 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

There total 3 articles about 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 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:

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (322479-18-5) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (214467-67-1)

Guidance literature:

With dimethyl sulfoxide; In acetic anhydride;

DOI:10.1016/S0040-4039(98)01540-8

Reference yield:

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide (55659-53-5,77790-47-7,93381-69-2,53270-13-6) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (214467-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / AgOTf, molecular sieves / CH₂Cl₂; toluene / -40 °C

2: 90 percent / K₂CO₃ / tetrahydrofuran; methanol

3: DMSO / acetic anhydride

With molecular sieve; silver trifluoromethanesulfonate; potassium carbonate; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; acetic anhydride; toluene;

DOI:10.1016/S0040-4039(98)01540-8

Reference yield:

Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester (214467-66-0) → 2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-oxo-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (214467-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / K₂CO₃ / tetrahydrofuran; methanol

2: DMSO / acetic anhydride

With potassium carbonate; dimethyl sulfoxide; In tetrahydrofuran; methanol; acetic anhydride;

DOI:10.1016/S0040-4039(98)01540-8

upstream raw materials:

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester

Downstream raw materials:

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3S,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-5-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

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