(Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate

Base Information

• Chemical Name: (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate
• CAS No.: 142955-64-4
• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.358
• Mol file: 142955-64-4.mol

Synonyms:(Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate

Chemical Property of (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate

There total 10 articles about (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate 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%

2,4-O-Isopropylidene-5-C-phenyl-D-gluco-pentose (164668-39-7) + methyl (triphenylphosphoranylidene)acetate (21204-67-1,2605-67-6) → (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate (142955-64-4) + (E)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate (142955-62-2)

Guidance literature:

In methanol; for 2h; Ambient temperature;

DOI:10.1039/c39920000810

Reference yield:

3,5:6,7-bis-O-(1-methylethylidene)-α-D-glucoheptonic γ-lactone (6605-22-7) → (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate (142955-64-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / 75percent aq. CH₃COOH / 24 h / Ambient temperature

2: 100 percent / NaIO₄ / methanol; H₂O / 1 h / Ambient temperature

3: 40 percent / diethyl ether / 4 h / Ambient temperature

4: 95 percent / NaIO₄ / methanol / 4 h / Ambient temperature

5: 90 percent / methanol / 2 h / Ambient temperature

With sodium periodate; acetic acid; In methanol; diethyl ether; water;

DOI:10.1039/c39920000810

Reference yield:

3,5-O-Isopropylidene-D-glycero-D-gulo-heptono-γ-lactone (6605-23-8) → (Z)-Methyl 4,6-O-isopropylidene-7-C-phenyl-D-gluco-hept-2-enoate (142955-64-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / NaIO₄ / methanol; H₂O / 1 h / Ambient temperature

2: 40 percent / diethyl ether / 4 h / Ambient temperature

3: 95 percent / NaIO₄ / methanol / 4 h / Ambient temperature

4: 90 percent / methanol / 2 h / Ambient temperature

With sodium periodate; In methanol; diethyl ether; water;

DOI:10.1039/c39920000810

upstream raw materials:

2,4-O-isopropylidene-5-C-phenyl-L-gluco-pentose

methyl (triphenylphosphoranylidene)acetate

2,4-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol

1,3-di-O-acetyl-2,4-O-isopropylidene-1-C-phenyl-D-glycero-D-gulo-hexitol

Downstream raw materials:

(Z)-7-C-phenyl-L-gluco-hept-2-enono-γ-lactone

4,6-O-Isopropylidene-7-C-phenyl-D-gluco-hept-2-enono-δ-lactone

(S)-5-((1S,2R,3R)-1,2,3-trihydroxy-3-phenylpropyl)furan-2(5H)-one