diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

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Chemical Name:diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate
CAS No.:338951-72-7
Molecular Formula:C₇₃H₁₂₁NO₉Si
Molecular Weight:1184.85
Hs Code.:

diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

Synonyms:diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

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Chemical Property of diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

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Technology Process of diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

There total 10 articles about diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-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%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 338951-71-6
diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

: 338951-72-7
diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1016/S0008-6215(01)00055-6

Reference yield:

: 354567-15-0
(4R)-2,4-diundexyl-1,3-dioxane

: 338951-72-7
diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 89 percent / DIBAL / CH₂Cl₂ / 5 h / 20 °C

2.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3.1: 73 percent / NaH / dimethylformamide / 20 h / 20 °C

4.1: 70 percent / SeO₂; AcOH / dioxane / 1 h / Heating

5.1: 91 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

6.1: 75 percent / 4A MS / CH₂Cl₂ / 1 h / 20 °C

7.1: PPh₃; NH₃ / tetrahydrofuran; H₂O / 24 h / 60 °C

8.1: 79 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

9.1: HCl; water / dioxane / 3 h / 60 °C

9.2: 50 percent / dimethylformamide / 1 h / 60 °C

10.1: 87 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

With hydrogenchloride; dmap; selenium(IV) oxide; ammonia; water; sodium hydride; diisobutylaluminium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00055-6

Reference yield:

: 354567-16-1
(4R)-3-dodecyloxy-1-hydroxytetradecane

: 338951-72-7
diphenylmethyl 2,6-anhydro-3-[(R)-3-(benzyloxy)tetradecanamido]-3-deoxy-7-O-tert-butyldimethylsilyl-4-O-[(R)-3-(dodecyloxy)tetradecyl]-D-glycero-D-ido-heptonate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 98 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 73 percent / NaH / dimethylformamide / 20 h / 20 °C

3.1: 70 percent / SeO₂; AcOH / dioxane / 1 h / Heating

4.1: 91 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

5.1: 75 percent / 4A MS / CH₂Cl₂ / 1 h / 20 °C

6.1: PPh₃; NH₃ / tetrahydrofuran; H₂O / 24 h / 60 °C

7.1: 79 percent / DCC; DMAP / CH₂Cl₂ / 18 h / 20 °C

8.1: HCl; water / dioxane / 3 h / 60 °C

8.2: 50 percent / dimethylformamide / 1 h / 60 °C

9.1: 87 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

With hydrogenchloride; dmap; selenium(IV) oxide; ammonia; water; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(01)00055-6