phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
• CAS No.: 89387-42-8
• Molecular Formula: C₃₅H₃₆O₆S
• Molecular Weight: 584.733
• Mol file: 89387-42-8.mol

Synonyms:phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

There total 13 articles about phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-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: 98.0%

acetic anhydride (108-24-7) + (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol (97974-20-4) → phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (89387-42-8)

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1016/S0008-6215(99)00131-7

Reference yield: 87.3%

1,4-di-O-acetyl-2,3,6-tri-O-benzyl-D-glucopyranoside (61236-93-9) + tetrabutyltin phenylsulfide → phenyl-4-O-acetyl-2,3,6-tri-O-benzyl-1-deoxy-1-thio-D-glucopyranoside (89387-41-7,89387-42-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h;

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → phenyl 4-O-acetyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (89387-42-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / CSA / benzene / 25 °C

2: 90 percent / NaH / tetrahydrofuran / Heating

3: 1.) NaCNBH₃, 4 A mol. sieves; 2.) HCl(g) / 1.) THF, 25 deg C; 2.) Et₂O

4: 95 percent / DMAP / CH₂Cl₂ / 0 - 25 °C

With hydrogenchloride; dmap; 4 A molecular sieve; camphor-10-sulfonic acid; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/ja00305a056

upstream raw materials:

1,4-di-O-acetyl-2,3,6-tri-O-benzyl-D-glucopyranoside

4-O-acetyl-2,3,6-tri-O-benzyl-β-D-glucopyranoside

acetic anhydride

(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Downstream raw materials:

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((S)-2-benzyloxy-1-methyl-ethoxy)-tetrahydro-pyran-3-yl ester

Acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((S)-2-benzyloxy-1-methyl-ethoxy)-tetrahydro-pyran-3-yl ester

1-O-benzyl-2-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-3-deoxy-2(S)-glycerol

Acetic acid (2R,3R,4S,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-((R)-2-benzyloxy-1-methyl-ethoxy)-tetrahydro-pyran-3-yl ester