methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside
• CAS No.: 131757-84-1
• Molecular Formula: C₃₅H₃₈O₅S
• Molecular Weight: 570.75
• Mol file: 131757-84-1.mol

Synonyms:methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside

Chemical Property of methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside

There total 18 articles about methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-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: 66.0%

(1S)-2,3,4,6-tetra-O-benzyl-L-idose S-acetyl O-methyl monothioacetal → methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside (131757-84-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In benzene; Ambient temperature;

DOI:10.1016/0008-6215(95)00386-X

Reference yield: 66.0%

methyl 2,3,4,6-tetra-O-benzyl-5-C-hydroxy-5-thio-α-D-glucopyranoside (139211-78-2) → methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside (131757-84-1)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate;

DOI:10.1016/0040-4039(91)85047-9

Reference yield: 11.0%

methyl 2,3,4,6-tetra-O-benzyl-5-C-hydroxy-5-thio-β-D-glucopyranoside (139342-66-8) → methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside (131757-84-1) + methyl 2,3,4,6-tetra-O-benzyl-5-thio-β-D-glucopyranoside (139183-49-6) + 1,5-anhydro-2,3,4,6-tetra-O-benzyl-5-thio-D-glucitol (176757-09-8)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃; for 1h; Product distribution; Mechanism; also α-anomer; var. acid (TFA), var. solvents, temperature and time;

DOI:10.1016/0008-6215(95)00386-X

upstream raw materials:

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

benzyl chloride

methyl 2,3,4,6-tetra-O-benzyl-5-C-hydroxy-5-thio-α-D-glucopyranoside

methyl 2,3,4,6-tetra-O-benzyl-5-C-hydroxy-5-thio-β-D-glucopyranoside

Downstream raw materials:

1-O-acetyl-2,3,4,6-tetra-O-benzyl-5-thio-α-D-glucopyranose

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one

5-(benzyloxymethyl)-thiophene-2-carboxaldehyde