2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside

Base Information

Chemical Name:2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside
CAS No.:592543-40-3
Molecular Formula:C₄₉H₈₂F₃NO₉
Molecular Weight:886.187
Hs Code.:

2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside

Synonyms:2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside

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Chemical Property of 2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside

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Technology Process of 2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside

There total 11 articles about 2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside 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: 85.0%

: 592543-39-0
2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-α-D-glycopyranoside

: 338952-07-1
1-methylsulfonyloxy-3-[(R)-[(Z)-tetradec-7-enyloxy]]tetradecane

: 592543-40-3
2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside

Guidance literature:: 2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-α-D-glycopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.25h;

1-methylsulfonyloxy-3-[(R)-[(Z)-tetradec-7-enyloxy]]tetradecane; In N,N-dimethyl-formamide; at 20 ℃; for 3h;
DOI:10.1246/bcsj.76.1011

Reference yield:

: 37043-40-6
2-(tetradec-7-yn-1-yloxy)tetrahydro-2H-pyran

: 592543-40-3
2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C

2.1: H₂ / Lindlar's catalyst / hexane / 9 h / 20 °C

3.1: 8.7 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 100 percent / D-10-camphorsulfonic acid / benzene / 2 h / 50 °C / 70 Torr

5.1: 81 percent / DIBAL / toluene / 10 h / 50 °C

6.1: 100 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 4 h / 20 °C

7.1: NaH / dimethylformamide / 0.25 h / 0 °C

7.2: 85 percent / dimethylformamide / 3 h / 20 °C

With oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1246/bcsj.76.1011

Reference yield:

: 53963-10-3
2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran

: 592543-40-3
2-(4-methoxybenzyloxy)ethyl 2-deoxy-4,6-O-isopropylidene-3-O-[(R)-3-[(Z)-tetradec-7-enyloxy]tetradecyl]-2-trifluoroacetamido-α-D-glycopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C

1.2: hexamethylphosphoric triamide (HMPA) / tetrahydrofuran; hexane / 22 h / 20 °C

2.1: 47.7 g / D-10-camphorsulfonic acid / methanol / 24 h / 20 °C

3.1: H₂ / Lindlar's catalyst / hexane / 9 h / 20 °C

4.1: 8.7 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / 0 °C

5.1: 100 percent / D-10-camphorsulfonic acid / benzene / 2 h / 50 °C / 70 Torr

6.1: 81 percent / DIBAL / toluene / 10 h / 50 °C

7.1: 100 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 4 h / 20 °C

8.1: NaH / dimethylformamide / 0.25 h / 0 °C

8.2: 85 percent / dimethylformamide / 3 h / 20 °C

With n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1246/bcsj.76.1011