2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone
• CAS No.: 131757-92-1
• Molecular Formula: C34H34O5S
• Molecular Weight: 554.707
• Mol file: 131757-92-1.mol

Synonyms:2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone;(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one

Chemical Property of 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone

There total 9 articles about 2,3,4,6-Tetra-O-benzyl-5-thio-D-glucono-1,5-lactone 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: 82.0%

2,3,4,6-tetra-O-benzyl-5-thio-D-glucopyranose → (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one (131757-92-1)

Guidance literature:

With acetic anhydride; dimethyl sulfoxide; at 20 ℃; for 12h;

Reference yield:

1,2,3,4,6-penta-O-acetyl-5-thio-α-D-glucopyranoside (10227-18-6) → (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one (131757-92-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 3 percent / 2.8percent HCl / H₂O / 34 h / Heating

2: 1.) NaH / 1.) DMF, 2.) RT

3: 50 percent / 1M H₂SO₄ / acetic acid / 4 h / 90 °C

4: 77 percent / DMSO/acetic anhydride / 42 h / Ambient temperature

With hydrogenchloride; sulfuric acid; acetic anhydride; sodium hydride; dimethyl sulfoxide; In water; acetic acid;

Reference yield:

3,6-di-O-acetyl-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose (10227-17-5) → (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one (131757-92-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 31 percent / 2.8percent HCl / H₂O / 5 h / Heating

2: 1.) NaH / 1.) DMF, 2.) RT

3: 50 percent / 1M H₂SO₄ / acetic acid / 4 h / 90 °C

4: 77 percent / DMSO/acetic anhydride / 42 h / Ambient temperature

With hydrogenchloride; sulfuric acid; acetic anhydride; sodium hydride; dimethyl sulfoxide; In water; acetic acid;

upstream raw materials:

1,2,3,4,6-penta-O-acetyl-5-thio-α-D-glucopyranoside

3,6-di-O-acetyl-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose

methyl 5-deoxy-5-thio-α-D-glucopiranoside

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-(1,3-dioxolan-2-yl)-4-methylphenyl]-5-thio-D-glucopyranose

(1S,3'R,4'S,5'S,6'R)-3',4',5'-tris(benzyloxy)-6'-(benzyloxymethyl)-3',4',5',6'-tetrahydro-6-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2'-[2H]thiopyran]

2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-(1,3-dioxolan-2-yl)-4-methylphenyl]-5-thio-D-glucopyranose

(2S,3R,4R,5S,6R)-2-(4-chloro-3-((2,3-dihydrobenzorbiri,41dioxin-6-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-3,4,5-triol