(2R,3S,4S,5R,6S)-6-(Benzooxazol-2-ylsulfanyl)-5-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-6-(Benzooxazol-2-ylsulfanyl)-5-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol
• CAS No.: 950902-50-8
• Molecular Formula: C₂₀H₂₁NO₆S
• Molecular Weight: 403.456

Synonyms:(2R,3S,4S,5R,6S)-6-(Benzooxazol-2-ylsulfanyl)-5-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Chemical Property of (2R,3S,4S,5R,6S)-6-(Benzooxazol-2-ylsulfanyl)-5-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

Chemical Property:

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Technology Process of (2R,3S,4S,5R,6S)-6-(Benzooxazol-2-ylsulfanyl)-5-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

There total 2 articles about (2R,3S,4S,5R,6S)-6-(Benzooxazol-2-ylsulfanyl)-5-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 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:

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide (29741-69-3) → (2R,3S,4S,5R,6S)-6-(Benzooxazol-2-ylsulfanyl)-5-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol (950902-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / K₂CO₃ / acetone; toluene / 16 h / 20 °C

2: MeONa / methanol

With sodium methylate; potassium carbonate; In methanol; acetone; toluene;

DOI:10.1021/ol0273452

Reference yield:

2-sulfanyl-1,3-benzoxazole (2382-96-9,118090-08-7) → (2R,3S,4S,5R,6S)-6-(Benzooxazol-2-ylsulfanyl)-5-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol (950902-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / K₂CO₃ / acetone; toluene / 16 h / 20 °C

2: MeONa / methanol

With sodium methylate; potassium carbonate; In methanol; acetone; toluene;

DOI:10.1021/ol0273452

Reference yield: 90.0%

(2R,3S,4S,5R,6S)-6-(Benzooxazol-2-ylsulfanyl)-5-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol (950902-50-8) + benzyl bromide (100-39-0) → benzoxazol-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (810670-73-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo071191s

upstream raw materials:

3,4,6-tetra-O-acetyl-2-O-benzyl-α-D-glucopyranosyl bromide

2-sulfanyl-1,3-benzoxazole

Downstream raw materials:

benzoxazol-2-yl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

2-(2'-O-benzyl-3',4',6'-tri-O-benzoyl-1-thio-β-D-glucopyranosyl)-benzoxazole

benzoxazol-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

benzoxazol-2-yl 3,4-di-O-acetyl-2-O-benzyl-1-thio-β-D-glucopyranoside

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