thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside

Base Information

• Chemical Name: thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside
• CAS No.: 196705-08-5
• Molecular Formula: C₄₅H₅₂O₁₂S
• Molecular Weight: 816.967

Synonyms:thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside

Chemical Property of thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside

Chemical Property:

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Technology Process of thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside

There total 2 articles about thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside 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:

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester (196704-63-9) → thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside (196705-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethyldioxirane / acetone; CH₂Cl₂

2: trifluoroacetic acid anhydride / CH₂Cl₂

With 3,3-dimethyldioxirane; trifluoroacetic anhydride; In dichloromethane; acetone; 1: Epoxidation / 2: Ring cleavage;

DOI:10.1021/ja971640d

Reference yield:

ethanethiol (75-08-1) + Acetic acid (2S,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(1aS,2aR,5R,6aR,7S,7aR)-5-(4-methoxy-phenyl)-hexahydro-1,2,4,6-tetraoxa-cyclopropa[b]naphthalen-7-yloxy]-tetrahydro-pyran-3-yl ester → thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside (196705-08-5)

Guidance literature:

With trifluoroacetic anhydride; In dichloromethane;

DOI:10.1021/ja971640d

Reference yield: 100.0%

pivaloyl chloride (3282-30-2) + thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-β-D-glucopyranoside (196705-08-5) → thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-2-O-pivaloyl-β-D-glucopyranoside (196705-11-0)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/ja971640d

upstream raw materials:

ethanethiol

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-[(2R,4aR,8R,8aS)-2-(4-methoxy-phenyl)-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester

Downstream raw materials:

thioethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->3)-4,6-O-(4-methoxy)benzylidene-2-O-pivaloyl-β-D-glucopyranoside

Acetic acid (2R,4aR,6S,7R,8S,8aR)-8-((2S,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-ethylsulfanyl-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Benzoic acid (2R,4aR,6S,7R,8S,8aR)-8-((2S,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-ethylsulfanyl-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

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