(3R,4R,5S)-3,4,5-Tris-benzyloxy-2-methoxy-tetrahydro-thiopyran 1,1-dioxide

Base Information

• Chemical Name: (3R,4R,5S)-3,4,5-Tris-benzyloxy-2-methoxy-tetrahydro-thiopyran 1,1-dioxide
• CAS No.: 330999-92-3
• Molecular Formula: C₂₇H₃₀O₆S
• Molecular Weight: 482.598

Synonyms:(3R,4R,5S)-3,4,5-Tris-benzyloxy-2-methoxy-tetrahydro-thiopyran 1,1-dioxide

Chemical Property of (3R,4R,5S)-3,4,5-Tris-benzyloxy-2-methoxy-tetrahydro-thiopyran 1,1-dioxide

Chemical Property:

Purity/Quality:

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Technology Process of (3R,4R,5S)-3,4,5-Tris-benzyloxy-2-methoxy-tetrahydro-thiopyran 1,1-dioxide

There total 1 articles about (3R,4R,5S)-3,4,5-Tris-benzyloxy-2-methoxy-tetrahydro-thiopyran 1,1-dioxide 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: 90.0%

methyl 2,3,4-tri-O-benzyl-5-thio-D-ribopyranose → (3R,4R,5S)-3,4,5-Tris-benzyloxy-2-methoxy-tetrahydro-thiopyran 1,1-dioxide (330999-92-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid;

DOI:10.1016/S0040-4039(00)02209-7

Reference yield: 52.0%

(3R,4R,5S)-3,4,5-Tris-benzyloxy-2-methoxy-tetrahydro-thiopyran 1,1-dioxide (330999-92-3) → C27H28O4 + C27H27ClO4 (330999-95-6)

Guidance literature:

With potassium hydroxide; In tetrachloromethane; tert-butyl alcohol; at 60 ℃;

DOI:10.1016/S0040-4039(00)02209-7

Reference yield:

(3R,4R,5S)-3,4,5-Tris-benzyloxy-2-methoxy-tetrahydro-thiopyran 1,1-dioxide (330999-92-3) → (4R,5R)-4,5-Bis-benzyloxy-cyclopent-2-enone

Guidance literature:

Multi-step reaction with 2 steps

1: 17 percent / KOH / CCl₄; 2-methyl-propan-2-ol / 60 °C

2: 85 percent / H₂SO₄ / tetrahydrofuran; H₂O / 12 h / 60 °C

With potassium hydroxide; sulfuric acid; In tetrahydrofuran; tetrachloromethane; water; tert-butyl alcohol; 1: Ramberg-Baecklund rearrangement;

DOI:10.1016/S0040-4039(00)02209-7

Downstream raw materials:

C₂₇H₂₇ClO₄

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