1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3-phenylthioureido)-α-D-glucopyranose

Base Information

• Chemical Name: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3-phenylthioureido)-α-D-glucopyranose
• CAS No.: 158315-51-6
• Molecular Formula: C₂₁H₂₆N₂O₉S
• Molecular Weight: 482.511

Synonyms:1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3-phenylthioureido)-α-D-glucopyranose

Chemical Property of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3-phenylthioureido)-α-D-glucopyranose

Chemical Property:

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Technology Process of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3-phenylthioureido)-α-D-glucopyranose

There total 1 articles about 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3-phenylthioureido)-α-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:

1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrochloride (10034-19-2,1191127-63-5) + phenyl isothiocyanate (103-72-0) → 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3-phenylthioureido)-α-D-glucopyranose (158315-51-6)

Guidance literature:

With calcium carbonate; Yield given. Multistep reaction; 1.) water, CH₂Cl₂, RT, 30 min; 2.) RT, 24 h;

DOI:10.1016/S0040-4020(01)81122-4

Reference yield: 92.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3-phenylthioureido)-α-D-glucopyranose (158315-51-6) → (4R,5R)-5-hydroxy-1-phenyl-4-(D-arabino-tetritol-1-yl)-imidazolidine-2-thione (158412-81-8)

Guidance literature:

With ammonia; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81122-4

Reference yield: 89.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(3-phenylthioureido)-α-D-glucopyranose (158315-51-6) → 2-phenylamino-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)<2,1-d>-2-thiazoline (158315-63-0)

Guidance literature:

With tin(IV) chloride; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81122-4

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose hydrochloride

phenyl isothiocyanate

Downstream raw materials:

(4R,5R)-5-hydroxy-1-phenyl-4-(D-arabino-tetritol-1-yl)-imidazolidine-2-thione

(4R,5R)-4-(4-O-acetyl-D-arabino-tetritol-1-yl)-1-phenyl-5-hydroxyimidazolidin-2-thione

2-phenylamino-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)<2,1-d>-2-thiazoline

(4R,5R)-1-phenyl-4-(1,3,4-tri-O-acetyl-D-arabino-tetritol-1-yl)-5-hydroxyimidazolidin-2-thione

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