Thioacetic acid S-((2S,3S,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester

Base Information

• Chemical Name: Thioacetic acid S-((2S,3S,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester
• CAS No.: 289898-46-0
• Molecular Formula: C₃₂H₃₆O₆S
• Molecular Weight: 548.7

Synonyms:Thioacetic acid S-((2S,3S,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester

Chemical Property of Thioacetic acid S-((2S,3S,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester

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Technology Process of Thioacetic acid S-((2S,3S,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester

There total 2 articles about Thioacetic acid S-((2S,3S,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester 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: 86.1%

potassium thioacetate (10387-40-3) + 1-O-allyl-2,3,4-tri-O-benzyl-β-D-glucose 6-O-tosylate (267900-41-4) → Thioacetic acid S-((2S,3S,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester (289898-46-0)

Guidance literature:

In ethanol; Heating;

DOI:10.1016/j.bmcl.2004.05.085

Reference yield:

allyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (89016-60-4) → Thioacetic acid S-((2S,3S,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester (289898-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 89.8 percent / pyridine; DMAP / 20 °C

2: 86.1 percent / ethanol / Heating

With pyridine; dmap; In ethanol;

DOI:10.1016/j.bmcl.2004.05.085

Reference yield: 74.7%

Thioacetic acid S-((2S,3S,4S,5R,6R)-6-allyloxy-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl) ester (289898-46-0) → Thioacetic acid S-[(2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl] ester (289898-47-1)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In tert-butyl alcohol; at 20 ℃;

DOI:10.1016/j.bmcl.2004.05.085

upstream raw materials:

potassium thioacetate

1-O-allyl-2,3,4-tri-O-benzyl-β-D-glucose 6-O-tosylate

allyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

Thioacetic acid S-[(2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl] ester

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