Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester
CAS No.:511274-74-1
Molecular Formula:C₂₅H₃₄O₇
Molecular Weight:446.541
Hs Code.:

Synonyms:Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester

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Technology Process of Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester

There total 8 articles about Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester 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: 98.0%

: 511274-43-4
(2R,3R,4S,5S,6S)-6-Benzyl-2-hydroxymethyl-4,5-dimethoxy-tetrahydro-pyran-3-ol

: 39716-58-0
pent-4-enoyl chloride

: 511274-74-1
Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jo051021k

Reference yield:

: 4196-35-4
2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide

: 511274-74-1
Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 48 percent / diethyl ether / 19 h

2: 99 percent / H₂ / Pd/C / ethanol / 2 h / 20 °C / 3040 Torr

3: 71 percent / 10-camphorsulfonic acid / dimethylformamide / 6 h / 110 °C

4: 91 percent / various solvent(s); 1,2-dimethoxy-ethane / 16 h

5: 99 percent / 10-camphorsulfonic acid / methanol / 2 h / 20 °C

6: 98 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 20 °C

With pyridine; dmap; (1S)-10-camphorsulfonic acid; hydrogen; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo051021k

Reference yield:

: 59531-24-7
2,3,4,6-tetra-O-benzyl-D-glucopyranoside

: 511274-74-1
Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: oxalyl bromide / CH₂Cl₂; dimethylformamide / 1 h / 20 °C

2: 48 percent / diethyl ether / 19 h

3: 99 percent / H₂ / Pd/C / ethanol / 2 h / 20 °C / 3040 Torr

4: 71 percent / 10-camphorsulfonic acid / dimethylformamide / 6 h / 110 °C

5: 91 percent / various solvent(s); 1,2-dimethoxy-ethane / 16 h

6: 99 percent / 10-camphorsulfonic acid / methanol / 2 h / 20 °C

7: 98 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 20 °C

With pyridine; dmap; Oxalyl bromide; (1S)-10-camphorsulfonic acid; hydrogen; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo051021k