diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate

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Chemical Name:diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate
CAS No.:214050-97-2
Molecular Formula:C₆₂H₈₇NO₁₀
Molecular Weight:1006.37
Hs Code.:

Synonyms:diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate

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Chemical Property of diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate

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Technology Process of diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate

There total 9 articles about diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate 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: 87.0%

: 214050-96-1
diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptonate

: 214050-97-2
diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 24 ℃; for 3h;
DOI:10.1016/S0040-4020(00)00684-0

Reference yield:

: 87357-67-3
(R)-3-benzyloxytetradecanoic acid

: 214050-97-2
diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate

Guidance literature:: Multi-step reaction with 6 steps

1: 14.6 g / DCC / CH₂Cl₂ / 1.5 h

2: aq. HCl / dioxane / 4 h / 60 °C

3: 897 mg / dimethylformamide / 2 h / 60 °C

4: 80 percent / p-TsOH / dimethylformamide / 3 h / 20 °C

5: 85 percent / DCC; DMAP / CH₂Cl₂ / 16 h / 24 °C

6: 87 percent / p-TsOH / methanol / 3 h / 24 °C

With hydrogenchloride; dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis / 3: Esterification / 4: cyclocondensation / 5: Esterification / 6: ether cleavage;
DOI:10.1016/S0040-4020(00)00684-0

Reference yield:

: 179530-53-1
2,6-anhydro-3-azido-3-deoxy-5,7-O-isopropylidene-D-glycero-D-ido-heptononitrile

: 214050-97-2
diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-4-O-[(R)-3-(benzyloxy)tetradecanoyl]-3-deoxy-D-glycero-D-ido-heptonate

Guidance literature:: Multi-step reaction with 8 steps

1: tetrahydrofuran / 2 h / 20 °C

2: aq. NH₃ / tetrahydrofuran / 3 h / 60 °C

3: 14.6 g / DCC / CH₂Cl₂ / 1.5 h

4: aq. HCl / dioxane / 4 h / 60 °C

5: 897 mg / dimethylformamide / 2 h / 60 °C

6: 80 percent / p-TsOH / dimethylformamide / 3 h / 20 °C

7: 85 percent / DCC; DMAP / CH₂Cl₂ / 16 h / 24 °C

8: 87 percent / p-TsOH / methanol / 3 h / 24 °C

With hydrogenchloride; dmap; ammonium hydroxide; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Hydrolysis / 3: Condensation / 4: Hydrolysis / 5: Esterification / 6: cyclocondensation / 7: Esterification / 8: ether cleavage;
DOI:10.1016/S0040-4020(00)00684-0