thioethyl 2-O-benzylcarbamoyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose

Base Information

• Chemical Name: thioethyl 2-O-benzylcarbamoyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose
• CAS No.: 316353-08-9
• Molecular Formula: C₃₄H₆₅NO₆SSi₃
• Molecular Weight: 700.216

Synonyms:thioethyl 2-O-benzylcarbamoyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose

Chemical Property of thioethyl 2-O-benzylcarbamoyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose

Chemical Property:

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Technology Process of thioethyl 2-O-benzylcarbamoyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose

There total 2 articles about thioethyl 2-O-benzylcarbamoyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose 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%

benzyl isothiocyanate (3173-56-6) + thioethyl 3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose (316352-68-8) → thioethyl 2-O-benzylcarbamoyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose (316353-08-9)

Guidance literature:

With pyridine; In dichloromethane; for 120h; Heating;

DOI:10.1021/jo001099v

Reference yield:

3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose (121654-00-0) → thioethyl 2-O-benzylcarbamoyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose (316353-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / trifluoroacetic anhydride / toluene / 48 h / 20 °C

2: 62 percent / pyridine / CH₂Cl₂ / 120 h / Heating

With pyridine; trifluoroacetic anhydride; In dichloromethane; toluene;

DOI:10.1021/jo001099v

Reference yield: 95.0%

thioethyl 2-O-benzylcarbamoyl-3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose (316353-08-9) → thioethyl 2-O-benzylcarbamoyl-β-D-glucopyranose (316353-10-3)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/jo001099v

upstream raw materials:

benzyl isothiocyanate

thioethyl 3,4,6-tri-O-(tert-butyldimethylsilyl)-β-D-glucopyranose

3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose

Downstream raw materials:

thioethyl 2-O-benzylcarbamoyl-β-D-glucopyranose

Isopropyl-carbamic acid (2S,3R,4S,5R,6R)-3-benzylcarbamoyloxy-2-ethylsulfanyl-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester

thioethyl 2-O-benzylcarbamoyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranose

2-bromoethyl 2-O-benzylcarbamoyl-3-O-isopropylcarbamoyl-β-D-glucopyranose

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