methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate

Base Information

• Chemical Name: methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate
• CAS No.: 130799-10-9
• Molecular Formula: C₂₉H₃₄O₆
• Molecular Weight: 478.585
• Mol file: 130799-10-9.mol

Synonyms:methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate

Chemical Property of methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate

There total 26 articles about methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate 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: 90.0%

{(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-[(E)-2-((1S,2S,3S)-2-hydroxymethyl-3-methyl-cyclopropyl)-vinyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester (153618-43-0) → methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate (130799-10-9)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)88025-X

Reference yield: 62.0%

((2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-{(Z)-2-[(1S,2S,3S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-methyl-cyclopropyl]-vinyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester → methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate (130799-10-9)

Guidance literature:

((2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-{(Z)-2-[(1S,2S,3S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-methyl-cyclopropyl]-vinyl}-tetrahydro-pyran-2-yl)-acetic acid methyl ester; hydrogenchloride; In methanol; at 20 ℃; for 1h;

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h;

With triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

Reference yield:

methyl 2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosiduronic acid (130799-00-7) → methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate (130799-10-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / diethyl ether / 0.5 h / 0 °C

2: 68 percent / 48 h / 30 °C / Irradiation

3: 1.) Ac₂O, H₂SO₄, 2.) MeONa / 1.) -20 deg C, 10 min, 2.) methanol, 0 deg C, 10 min

4: 92 percent / Et₂NSF₃ / CH₂Cl₂ / 0.17 h / -30 °C

5: 49 percent / toluene / 0.5 h / -20 - 20 °C

6: 1.) pTSA, 2.) Dess-Martin's periodinane / 1.) MeOH, CH₂Cl₂, RT, 2 h, 2.) CH₂Cl₂, RT, 30 min

With diethylamino-sulfur trifluoride; sulfuric acid; sodium methylate; acetic anhydride; Dess-Martin periodane; toluene-4-sulfonic acid; In diethyl ether; dichloromethane; toluene;

upstream raw materials:

methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-triphenylmethoxymethylcyclopropylethenyl>-D-glucoheptopyranuronate

{(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-[(E)-2-((1S,2S,3S)-2-hydroxymethyl-3-methyl-cyclopropyl)-vinyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester

menthyl (1S,2S,3S)-2-hydroxymethyl-3-methylcyclopropane-1-carboxylate

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde

Downstream raw materials:

methyl 5β,6α-dibenzyloxypolyangioate

5β,6α-dibenzyloxypolyangioic acid

(+)-ambruticin S