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

Base Information

• Chemical Name: (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol
• CAS No.: 200191-55-5
• Molecular Formula: C₂₀H₂₄O₄S
• Molecular Weight: 360.474

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

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

Chemical Property:

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

There total 10 articles about (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-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: 90.0%

Benzoic acid (2S,3S,4R,5S)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-thiopyran-2-ylmethyl ester (200191-60-2) → (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol (200191-55-5)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

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

Reference yield: 75.0%

(3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-bromomethyl-tetrahydro-thiopyran-3-ol (200191-59-9) → (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol (200191-55-5)

Guidance literature:

With silver nitrate; bis(tri-n-butyltin)oxide; In N,N-dimethyl-formamide; at 60 ℃; for 19h;

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

Reference yield: 75.0%

1,2:5,6-Dianhydro-3,4-di-O-benzyl-D-mannitol (157363-85-4) → (3S,4R,5R,6S)-4,5-Bis-benzyloxy-thiepane-3,6-diol (171667-67-7) + (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol (200191-55-5)

Guidance literature:

With sodium sulfide; In ethanol; Yields of byproduct given; Heating;

DOI:10.1016/0040-4039(95)01273-K

upstream raw materials:

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

Benzoic acid (2S,3S,4R,5S)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-thiopyran-2-ylmethyl ester

2,6-di-O-benzoyl-3,4-di-O-benzyl-1,5-dideoxy-1,5-thio-L-gulitol

Downstream raw materials:

(1S,3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-1-oxo-hexahydro-1λ⁴-thiopyran-3-ol

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

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