Methyl 3,4-anhydro-6-O-(tert-butyldiphenylsilyl)-2-O-(methanesulfonyl)-α-D-allopyranoside

Base Information

• Chemical Name: Methyl 3,4-anhydro-6-O-(tert-butyldiphenylsilyl)-2-O-(methanesulfonyl)-α-D-allopyranoside
• CAS No.: 172603-06-4
• Molecular Formula: C₂₄H₃₂O₇SSi
• Molecular Weight: 492.665
• Mol file: 172603-06-4.mol

Synonyms:Methyl 3,4-anhydro-6-O-(tert-butyldiphenylsilyl)-2-O-(methanesulfonyl)-α-D-allopyranoside

Chemical Property of Methyl 3,4-anhydro-6-O-(tert-butyldiphenylsilyl)-2-O-(methanesulfonyl)-α-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 3,4-anhydro-6-O-(tert-butyldiphenylsilyl)-2-O-(methanesulfonyl)-α-D-allopyranoside

There total 1 articles about Methyl 3,4-anhydro-6-O-(tert-butyldiphenylsilyl)-2-O-(methanesulfonyl)-α-D-allopyranoside 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: 59.0%

methyl 6-O-tert-butyldiphenylsilyl-2,3-di-O-methanesulfonyl-α-D-glucopyranoside (137963-61-2) → Methyl 3,4-anhydro-6-O-(tert-butyldiphenylsilyl)-2-O-(methanesulfonyl)-α-D-allopyranoside (172603-06-4)

Guidance literature:

With sodium methylate; In methanol; chloroform; at 25 ℃; for 120h;

DOI:10.1021/jo00128a032

Reference yield:

Methyl 3,4-anhydro-6-O-(tert-butyldiphenylsilyl)-2-O-(methanesulfonyl)-α-D-allopyranoside (172603-06-4) → (2S,3R,4R,5R,6R,5'S,6'R,7'R,8'R)-(2'E)-9'-<3,4-Bis(benzyloxy)-5-ethyl-tetrahydro-2-methoxy-2H-pyran-6-yl>-6'-methoxy-8'-<(methoxymethyl)oxy>-5',7'-dimethyl-2'-nonene (172603-22-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) CuCl / 1.) ether, THF, -30 deg C, 20 min, 2.) -30 deg C, 20 min; 0 deg C, 40 min

2: 81 percent / NaH / dimethylformamide / 4 h / 20 °C

3: 97 percent / n-Bu₄NF / tetrahydrofuran / 2.5 h / 25 °C

4: DMSO, (COCl)2 / CH₂Cl₂ / -78 - 0 °C

5: n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to -40 deg C, 2.) 20 deg C, 3 h

6: 1.) B₂H₆*THF, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 15-20 deg C, 30 min, 2.) EtOH, 40 deg C, 30 min

7: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 1.) 25 deg C, 5 h, 2.) 40 deg C, 2.5 h

8: 99 percent / nBu₄NF / tetrahydrofuran / 2.5 h / 25 °C

9: DMSO, (COCl)2 / CH₂Cl₂ / 0.5 h / -78 °C

10: t-BuOK / tetrahydrofuran / 1.) 25 deg C, 1.5 h, 2.) 55 deg C, 1 h

11: methanol / 2 h / 25 °C

12: NaBH₄, AcOH / 2 h / 25 °C

With sodium hydroxide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; B₂H₆-THF; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; acetic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; copper(l) chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00128a032

Reference yield:

Methyl 3,4-anhydro-6-O-(tert-butyldiphenylsilyl)-2-O-(methanesulfonyl)-α-D-allopyranoside (172603-06-4) → Methyl 2,3-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-4-deoxy-4-C-ethyl-α-D-gulopyranoside (172603-08-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) CuCl / 1.) ether, THF, -30 deg C, 20 min, 2.) -30 deg C, 20 min; 0 deg C, 40 min

2: 81 percent / NaH / dimethylformamide / 4 h / 20 °C

With sodium hydride; copper(l) chloride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00128a032

upstream raw materials:

methyl 6-O-tert-butyldiphenylsilyl-2,3-di-O-methanesulfonyl-α-D-glucopyranoside

Downstream raw materials:

Methyl 6-O-(tert-butyldiphenylsilyl)-4-deoxy-4-C-ethyl-α-D-gulopyranoside

pironetin

Methyl 2,3-di-O-benzyl-6-dehydro-4-deoxy-4-C-ethyl-α-D-gulopyranoside

Methyl 2,3-di-O-benzyl-4-deoxy-4-C-ethyl-α-D-gulopyranoside