dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 504422-56-4
• Molecular Formula: C₅₇H₇₈O₁₅S₂
• Molecular Weight: 1067.37
• Mol file: 504422-56-4.mol

Synonyms:

Chemical Property of dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

There total 16 articles about dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-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:

dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside (66854-07-7,103129-55-1,117076-31-0) → dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (504422-56-4)

Guidance literature:

Multi-step reaction with 12 steps

1: NaOMe / methanol / 20 °C

2: p-TsOH*H₂O / dimethylformamide / 4.5 h / 50 °C

3: 10.1 g / NaH / dimethylformamide / 0 - 20 °C

4: 95 percent / BH₃*Et₂O; AlCl₃; molecular sieves / tetrahydrofuran / 21 h / 20 °C

5: 96 percent Turnov_. / NaH; 15-crown-5 / dimethylformamide / 120 h / 70 °C

6: 100 percent / pyridine / 20 °C

7: 98 percent / DMSO; Ac₂O / 11 h / 20 °C

8: 67 percent / DBU / toluene / 1 h / 70 °C

9: 220 mg / BH₃*Et₂O / tetrahydrofuran / 16 h / 0 - 20 °C

10: 136 mg / pyridine / 20 °C

11: 805 mg / aq. AcOH / 10 h / 70 °C

12: 888 mg / pyridine / 14 h / 0 - 20 °C

With pyridine; aluminium trichloride; molecular sieve; tetrafluoroboric acid-diethyl ether complex; 15-crown-5; sodium methylate; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0008-6215(02)00294-X

Reference yield:

1-dodecyl alcohol (112-53-8) → dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (504422-56-4)

Guidance literature:

Multi-step reaction with 13 steps

1: silver perchlorate; silver carbonate; molecular sieves / CH₂Cl₂

2: NaOMe / methanol / 20 °C

3: p-TsOH*H₂O / dimethylformamide / 4.5 h / 50 °C

4: 10.1 g / NaH / dimethylformamide / 0 - 20 °C

5: 95 percent / BH₃*Et₂O; AlCl₃; molecular sieves / tetrahydrofuran / 21 h / 20 °C

6: 96 percent Turnov_. / NaH; 15-crown-5 / dimethylformamide / 120 h / 70 °C

7: 100 percent / pyridine / 20 °C

8: 98 percent / DMSO; Ac₂O / 11 h / 20 °C

9: 67 percent / DBU / toluene / 1 h / 70 °C

10: 220 mg / BH₃*Et₂O / tetrahydrofuran / 16 h / 0 - 20 °C

11: 136 mg / pyridine / 20 °C

12: 805 mg / aq. AcOH / 10 h / 70 °C

13: 888 mg / pyridine / 14 h / 0 - 20 °C

With pyridine; aluminium trichloride; molecular sieve; tetrafluoroboric acid-diethyl ether complex; 15-crown-5; sodium methylate; silver perchlorate; acetic anhydride; sodium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0008-6215(02)00294-X

Reference yield:

benzyl bromide (100-39-0) → dodecyl 2-O-acetyl-3-O-benzyl-4,6-di-O-methanesulfonyl-5a-carba-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (504422-56-4)

Guidance literature:

Multi-step reaction with 9 steps

1: NaH / dimethylformamide / 0 - 20 °C

2: 96 percent Turnov_. / NaH; 15-crown-5 / dimethylformamide / 120 h / 70 °C

3: 100 percent / pyridine / 20 °C

4: 98 percent / DMSO; Ac₂O / 11 h / 20 °C

5: 67 percent / DBU / toluene / 1 h / 70 °C

6: 220 mg / BH₃*Et₂O / tetrahydrofuran / 16 h / 0 - 20 °C

7: 136 mg / pyridine / 20 °C

8: 805 mg / aq. AcOH / 10 h / 70 °C

9: 888 mg / pyridine / 14 h / 0 - 20 °C

With pyridine; tetrafluoroboric acid-diethyl ether complex; 15-crown-5; acetic anhydride; sodium hydride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0008-6215(02)00294-X

upstream raw materials:

methanesulfonyl chloride

dodecyl 2,3,4,6-tetra-O-acetyl-α,β-D-glucopyranoside

1-dodecyl alcohol

benzyl bromide

Downstream raw materials:

dodecyl 2,3,4,6-tetra-O-acetyl-3-O-benzyl-5a-carba-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside

Refernces