((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-yl)-methanethiol

Base Information

• Chemical Name: ((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-yl)-methanethiol
• CAS No.: 193898-28-1
• Molecular Formula: C₃₅H₄₆O₅S
• Molecular Weight: 578.813

Synonyms:((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-yl)-methanethiol

Chemical Property of ((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-yl)-methanethiol

Chemical Property:

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Technology Process of ((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-yl)-methanethiol

There total 2 articles about ((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-yl)-methanethiol 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: 96.0%

Thioacetic acid S-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethyl) ester (193898-37-2) → ((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-yl)-methanethiol (193898-28-1)

Guidance literature:

With sodium methylate; In methanol; for 0.5h; Ambient temperature;

DOI:10.1139/v97-095

Reference yield:

octyl 2,3,4-tri-O-benzyl-6-O-methanesulfonyl-β-D-glucopyranoside (193898-36-1) → ((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-yl)-methanethiol (193898-28-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / dimethylformamide / 16 h / Ambient temperature

2: 96 percent / NaOMe / methanol / 0.5 h / Ambient temperature

With sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1139/v97-095

Reference yield:

1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose (74372-90-0,112289-38-0,135202-48-1,148888-66-8,71696-32-7) + ((2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-yl)-methanethiol (193898-28-1) → (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethylsulfanyl)-tetrahydro-pyran-3-ol (193898-38-3)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) THF, RT, 30 min, 2.) DMF, RT, 1 h;

DOI:10.1139/v97-095

upstream raw materials:

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

octyl 2,3,4-tri-O-benzyl-6-O-methanesulfonyl-β-D-glucopyranoside

Downstream raw materials:

(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethylsulfanyl)-tetrahydro-pyran-3-ol

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