(7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-one

Base Information

Chemical Name:(7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-one
CAS No.:117941-12-5
Molecular Formula:C₂₅H₃₉NO₇
Molecular Weight:465.587
Hs Code.:

Synonyms:(7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-one

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Chemical Property of (7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-one

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Technology Process of (7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-one

There total 10 articles about (7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-one 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: 80.0%

: 117941-13-6,118014-65-6,118014-66-7,119905-35-0
((1S,2S,3S)-1-Butyl-4-hydroxy-2,3-bis-methoxymethoxy-non-8-enyl)-carbamic acid benzyl ester

: 117941-12-5
(7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/ja00186a038

Reference yield:

: 117941-00-1
(2S,3R)-1-(Benzyloxy)-2,3-bis<(methoxymethyl)oxy>octan-4-one

: 117941-12-5
(7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-one

Guidance literature:: Multi-step reaction with 8 steps

1: 75 percent / 1 M LiBH(sec-Bu)3 / tetrahydrofuran / 1 h / -78 °C

2: 51 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

3: 76 percent / H₂ / 10percent Pd/C / methanol / 3 h

4: 86 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

5: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min

6: hydrazine hydrate / ethanol / 2 h / Heating

7: aq. Na₂CO₃ / CH₂Cl₂ / 0.08 h / 0 °C

8: 80 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

With oxalyl dichloride; hydrogen; L-Selectride; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/ja00186a038

Reference yield:

: 99878-63-4
4-O-benzyl-2,3-O-bis(methoxymethyl)-L-threose

: 117941-12-5
(7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-one

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) Mg / 1.) Et₂O, 2.) Et₂O, room temp., 14 h

2: 95 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

3: 75 percent / 1 M LiBH(sec-Bu)3 / tetrahydrofuran / 1 h / -78 °C

4: 51 percent / triphenyl phosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

5: 76 percent / H₂ / 10percent Pd/C / methanol / 3 h

6: 86 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

7: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min

8: hydrazine hydrate / ethanol / 2 h / Heating

9: aq. Na₂CO₃ / CH₂Cl₂ / 0.08 h / 0 °C

10: 80 percent / oxalyl chloride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

With oxalyl dichloride; hydrogen; L-Selectride; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/ja00186a038