p-tolyl 3,4,6-tri-O-benzyl-2-C-(formylmethyl)-2-deoxy-β-D-thioglucopyranoside

Base Information

• Chemical Name: p-tolyl 3,4,6-tri-O-benzyl-2-C-(formylmethyl)-2-deoxy-β-D-thioglucopyranoside
• CAS No.: 1319719-00-0
• Molecular Formula: C₃₆H₃₈O₅S
• Molecular Weight: 582.761
• Mol file: 1319719-00-0.mol

Synonyms:p-tolyl 3,4,6-tri-O-benzyl-2-C-(formylmethyl)-2-deoxy-β-D-thioglucopyranoside

Chemical Property of p-tolyl 3,4,6-tri-O-benzyl-2-C-(formylmethyl)-2-deoxy-β-D-thioglucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tolyl 3,4,6-tri-O-benzyl-2-C-(formylmethyl)-2-deoxy-β-D-thioglucopyranoside

There total 1 articles about p-tolyl 3,4,6-tri-O-benzyl-2-C-(formylmethyl)-2-deoxy-β-D-thioglucopyranoside 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: 70.0%

para-thiocresol (106-45-6) + 2-C-(3,4,6-tri-O-benzyl-2-O-tosyl-α-D-mannopyranosyl)acetaldehyde (780767-31-9) → p-tolyl 3,4,6-tri-O-benzyl-2-C-(formylmethyl)-2-deoxy-β-D-thioglucopyranoside (1319719-00-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol201622t

Reference yield: 88.0%

p-tolyl 3,4,6-tri-O-benzyl-2-C-(formylmethyl)-2-deoxy-β-D-thioglucopyranoside (1319719-00-0) + methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (76375-66-1) → (2R,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(methyl-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranos-3-yloxy)hexahydrofuro[2,3-b]pyran (1319719-13-5)

Guidance literature:

With N-iodo-succinimide; In dichloromethane; at -30 - 20 ℃; for 2h; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/ol201622t

Reference yield: 87.0%

p-tolyl 3,4,6-tri-O-benzyl-2-C-(formylmethyl)-2-deoxy-β-D-thioglucopyranoside (1319719-00-0) + isopropyl alcohol (67-63-0,8013-70-5) → (2S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-isopropoxyhexahydrofuro[2,3-b]pyran (1319719-05-5)

Guidance literature:

With N-iodo-succinimide; In dichloromethane; at -30 - 20 ℃; for 2h; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1021/ol201622t

upstream raw materials:

para-thiocresol

2-C-(3,4,6-tri-O-benzyl-2-O-tosyl-α-D-mannopyranosyl)acetaldehyde

Downstream raw materials:

(2R,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(furan-2-ylmethoxy)hexahydrofuro[2,3-b]pyran

(2R,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methoxyhexahydrofuro[2,3-b]pyran

(2S,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-methoxyhexahydrofuro[2,3-b]pyran

(2R,3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-(4-nitrophenoxy)hexahydrofuro[2,3-b]pyran