allyl 2,4,6-tri-O-benzyl-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-D-glucopyranoside

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Chemical Name:allyl 2,4,6-tri-O-benzyl-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-D-glucopyranoside
CAS No.:929619-18-1
Molecular Formula:C₄₆H₆₀O₇
Molecular Weight:724.978
Hs Code.:

Synonyms:allyl 2,4,6-tri-O-benzyl-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-D-glucopyranoside

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Chemical Property of allyl 2,4,6-tri-O-benzyl-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-D-glucopyranoside

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Technology Process of allyl 2,4,6-tri-O-benzyl-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-D-glucopyranoside

There total 6 articles about allyl 2,4,6-tri-O-benzyl-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-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: 56.0%

: 929619-17-0
1,2:5,6-di-O-isopropylidene-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-α-D-glucofuranoside

: 100-39-0
benzyl bromide

: 107-18-6
allyl alcohol

: 929619-18-1
allyl 2,4,6-tri-O-benzyl-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-D-glucopyranoside

Guidance literature:: 1,2:5,6-di-O-isopropylidene-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-α-D-glucofuranoside; With acetic acid; In water; at 105 ℃; for 5h;

allyl alcohol; With acetyl chloride; In water; for 24h; Heating;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 40h;
DOI:10.1021/jo061280p

Reference yield:

: 929619-00-1
5-(adamantan-1-yl-methoxy)-1-benzyloxy-pentane

: 929619-18-1
allyl 2,4,6-tri-O-benzyl-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / H₂ / Pd/C / ethanol / 20 h / 20 °C / 3750.3 Torr

2.1: 94 percent / CBr₄; PPh₃ / acetonitrile / 2.25 h / Heating

3.1: 98 percent / NaH / dimethylformamide / 6 h / 0 - 20 °C

4.1: AcOH / H₂O / 5 h / 105 °C

4.2: AcCl / H₂O / 24 h / Heating

4.3: 56 percent / NaH / dimethylformamide / 40 h / 0 - 20 °C

With carbon tetrabromide; hydrogen; sodium hydride; acetic acid; triphenylphosphine; palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide; acetonitrile; 4.2: Fisher glycosidation;
DOI:10.1021/jo061280p

Reference yield:

: 770-71-8
1-adamantanemethanol

: 929619-18-1
allyl 2,4,6-tri-O-benzyl-3-O-[5-(adamantan-1-yl-methoxy)-pentyl]-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 1.5 h / 20 °C

1.2: 92 percent / dimethylformamide / 1 h / 75 °C

2.1: 97 percent / H₂ / Pd/C / ethanol / 20 h / 20 °C / 3750.3 Torr

3.1: 94 percent / CBr₄; PPh₃ / acetonitrile / 2.25 h / Heating

4.1: 98 percent / NaH / dimethylformamide / 6 h / 0 - 20 °C

5.1: AcOH / H₂O / 5 h / 105 °C

5.2: AcCl / H₂O / 24 h / Heating

5.3: 56 percent / NaH / dimethylformamide / 40 h / 0 - 20 °C

With carbon tetrabromide; hydrogen; sodium hydride; acetic acid; triphenylphosphine; palladium on activated charcoal; In ethanol; water; N,N-dimethyl-formamide; acetonitrile; 5.2: Fisher glycosidation;
DOI:10.1021/jo061280p