(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ol

Base Information

• Chemical Name: (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ol
• CAS No.: 200191-81-7
• Molecular Formula: C₂₀H₂₄O₆S
• Molecular Weight: 392.473

Synonyms:(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ol

Chemical Property of (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ol

Chemical Property:

Purity/Quality:

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Technology Process of (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ol

There total 6 articles about (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1,1-dioxo-hexahydro-1λ⁶-thiopyran-3-ol 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: 89.0%

(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol (200191-55-5) → (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1,1-dioxo-hexahydro-1λ6-thiopyran-3-ol (200191-81-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; calcium carbonate; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4020(97)10096-5

Reference yield:

1,2:5,6-Dianhydro-3,4-di-O-benzyl-D-mannitol (157363-85-4) → (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1,1-dioxo-hexahydro-1λ6-thiopyran-3-ol (200191-81-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / sodium sulfide nonahydrate / ethanol / Heating

2: 80 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C

3: 90 percent / K₂CO₃ / methanol / 20 °C

4: 89 percent / calcium carbonate, meta-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

With sodium sulfide; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; calcium carbonate; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4020(97)10096-5

Reference yield:

benzoic acid (65-85-0,8013-63-6) → (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1,1-dioxo-hexahydro-1λ6-thiopyran-3-ol (200191-81-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 18 h / Ambient temperature

2: K₂CO₃ / methanol / 20 °C

3: 89 percent / calcium carbonate, meta-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

With potassium carbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; calcium carbonate; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4020(97)10096-5

upstream raw materials:

(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol

benzoic acid

1,2:5,6-Dianhydro-3,4-di-O-benzyl-D-mannitol

(3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-bromomethyl-tetrahydro-thiopyran-3-ol

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