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

Base Information

Chemical Name:(6R,7S,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-ol
CAS No.:118014-65-6
Molecular Formula:C₂₅H₄₁NO₇
Molecular Weight:467.603
Hs Code.:

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

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

Chemical Property:

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

There total 20 articles about (6R,7S,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-ol 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: 77.0%

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

: 118014-65-6
(6R,7S,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-ol

: 117941-13-6
(6S,7R,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-ol

Guidance literature:: With zinc(II) tetrahydroborate; In diethyl ether; at 0 ℃; for 0.75h; Yields of byproduct given;
DOI:10.1021/ja00186a038

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

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:

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

: 118014-65-6
(6R,7S,8S,9S)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-ol

Guidance literature:: Multi-step reaction with 9 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

9: 0.14 M Zn(BH₄)2 / diethyl ether / 0.75 h / 0 °C

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