methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 120315-58-4
• Molecular Formula: C₇₄H₇₉NO₁₄S
• Molecular Weight: 1238.51
• Mol file: 120315-58-4.mol

Synonyms:methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

There total 12 articles about methyl O--(2->6)-2,3,4-tri-O-benzyl-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: 71.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + (3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (120308-52-3) → methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (120315-58-4)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In tetrachloromethane; at 40 ℃; for 40h;

DOI:10.1016/S0040-4039(00)80400-1

Reference yield: 71.0%

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-chloro-2,3,5-trideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate (120308-52-3,128705-82-8) + methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside (4356-80-3,34212-64-1,40653-32-5,53008-65-4,68027-27-0,73111-53-2,128184-63-4,138794-99-7,55094-38-7,641635-63-4) → methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (120315-58-4)

Guidance literature:

With mercury(II) cyanide; mercury dibromide; In tetrachloromethane; at 30 ℃; for 72h; molecular sieves;

DOI:10.1016/S0040-4020(01)97586-6

Reference yield:

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3,5-trideoxy-2-fluoro-3-phenylseleno-D-erythro-α-L-gluco-nonulopyranosate (116096-67-4,116180-63-3,125356-39-0,125356-40-3,128658-86-6) → methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (120315-58-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 19 percent / AgOSO₂CF₃, SnCl₂ / CCl₄ / molecular sieves; -20 deg, 30 min, then 0 deg C, 30 min, then room temp., 2h

2: 78 percent / N-bromosuccinimide / acetonitrile; H₂O / 0.5 h / 60 °C

3: 4.23 g / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 0 deg C, 2h, then room temp., 1h

4: DBU / toluene / 0 deg C, 2h, then room temp., 30 min.

5: 99 percent / (Me₂N)3P, CCl₄ / tetrahydrofuran / -78 deg C -> room temp. (3h)

6: 71 percent / Hg(CN)2, HgBr₂ / CCl₄ / 72 h / 30 °C / molecular sieves

With tetrachloromethane; N-Bromosuccinimide; potassium tert-butylate; silver trifluoromethanesulfonate; mercury(II) cyanide; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dibromide; tin(ll) chloride; Hexamethylphosphorous triamide; In tetrahydrofuran; tetrachloromethane; water; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)97586-6

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

(3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2-chloro-2,3,5-trideoxy-3-phenylthio-D-erythro-β-L-gluco-2-nonulopyranosonate

methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside

Downstream raw materials:

methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside