methyl (R)-4,6-O-benzylidene-2-C-ethenyl-2-O-propenyl-3-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl (R)-4,6-O-benzylidene-2-C-ethenyl-2-O-propenyl-3-deoxy-α-D-glucopyranoside
• CAS No.: 220460-39-9
• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.397

Synonyms:methyl (R)-4,6-O-benzylidene-2-C-ethenyl-2-O-propenyl-3-deoxy-α-D-glucopyranoside

Chemical Property of methyl (R)-4,6-O-benzylidene-2-C-ethenyl-2-O-propenyl-3-deoxy-α-D-glucopyranoside

Chemical Property:

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Technology Process of methyl (R)-4,6-O-benzylidene-2-C-ethenyl-2-O-propenyl-3-deoxy-α-D-glucopyranoside

There total 2 articles about methyl (R)-4,6-O-benzylidene-2-C-ethenyl-2-O-propenyl-3-deoxy-α-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: 77.0%

allyl bromide (106-95-6) + methyl (R)-4,6-O-benzylidene-2-C-ethenyl-3-deoxy-α-D-glucopyranoside (220460-38-8) → methyl (R)-4,6-O-benzylidene-2-C-ethenyl-2-O-propenyl-3-deoxy-α-D-glucopyranoside (220460-39-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1002/(SICI)1521-3773(19981217)37:23<3298::AID-ANIE3298>3.0.CO;2-O

Reference yield:

methyl 4,6-O-(phenylmethylene)-3-deoxy-α-D-erythro-hexopyranoside-2-ulose (74524-02-0) → methyl (R)-4,6-O-benzylidene-2-C-ethenyl-2-O-propenyl-3-deoxy-α-D-glucopyranoside (220460-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / tetrahydrofuran / 2 h / Heating

2: 77 percent / NaH; DMPU / tetrahydrofuran / 4 h / Heating

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydride; In tetrahydrofuran; 1: Addition / 2: Etherification;

DOI:10.1021/jo991392z

Reference yield: 86.0%

methyl (R)-4,6-O-benzylidene-2-C-ethenyl-2-O-propenyl-3-deoxy-α-D-glucopyranoside (220460-39-9) → methyl (R)-4,6-O-benzylidene-2,3-dideoxy-2(S)-spiro(2,7'-3'(R),6'(R)-1'-oxa-bicyclo[3.2.0]heptane)-α-D-glucopyranoside

Guidance literature:

With copper(I) trifluoromethanesulfonate benzene; In benzene; for 8h; Irradiation;

DOI:10.1039/b315623k

upstream raw materials:

allyl bromide

methyl (R)-4,6-O-benzylidene-2-C-ethenyl-3-deoxy-α-D-glucopyranoside

methyl 4,6-O-(phenylmethylene)-3-deoxy-α-D-erythro-hexopyranoside-2-ulose

Downstream raw materials:

methyl (R)-4,6-O-benzylidene-2(S)-spiro(2,5'-2',5'-dihydrofuran)-2,3-dideoxy-α-D-glucopyranoside

methyl (R)-4,6-O-benzylidene-2(R)-spiro(2,5'-2',3',4',5'-tetrahydrofuran)-2,3-dideoxy-α-D-glucopyranoside

methyl (R)-4-O-benzoyl-6-C-bromo-2(R)-spiro(2,5'-2',3',4',5'-tetrahydrofuran)-2,3,6-trideoxy-α-D-glucopyranoside

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