(2S,3S,4S,5R)-5-<<(benzyloxy)carbonyl>amino>-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-2-pentanol

Base Information

Chemical Name:(2S,3S,4S,5R)-5-<<(benzyloxy)carbonyl>amino>-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-2-pentanol
CAS No.:108394-49-6
Molecular Formula:C₂₄H₃₃NO₈
Molecular Weight:463.528
Hs Code.:

Synonyms:(2S,3S,4S,5R)-5-<<(benzyloxy)carbonyl>amino>-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-2-pentanol

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Chemical Property of (2S,3S,4S,5R)-5-<<(benzyloxy)carbonyl>amino>-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-2-pentanol

Chemical Property:

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Technology Process of (2S,3S,4S,5R)-5-<<(benzyloxy)carbonyl>amino>-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-2-pentanol

There total 9 articles about (2S,3S,4S,5R)-5-<<(benzyloxy)carbonyl>amino>-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-2-pentanol 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:

: 99878-64-5
(1R,2S,3S)-4-(benzyloxy)-2,3-bis<(methoxymethyl)oxy>-1-(p-methoxyphenyl)-1-butanol

: 108394-49-6
(2S,3S,4S,5R)-5-<<(benzyloxy)carbonyl>amino>-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-2-pentanol

Guidance literature:: Multi-step reaction with 8 steps

1: 32 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 12 h / Ambient temperature

2: 75 percent / H₂ / 10percent Pd on C / methanol / 3.5 h / 760 Torr

3: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 - 20 deg C

4: 1.) Mg / 1.) Et₂O, 2.) Et₂O, -78 deg C, 2 h

5: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 - 20 deg C

6: 60 percent / NaBH₄ / ethanol / 1 h / 0 °C

7: hydrazine hydrate / ethanol / 2.5 h / Heating

8: Na₂CO₃ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With sodium tetrahydroborate; oxalyl dichloride; hydrogen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;
DOI:10.1021/jo00386a012

Reference yield:

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

: 108394-49-6
(2S,3S,4S,5R)-5-<<(benzyloxy)carbonyl>amino>-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-2-pentanol

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) Mg / 1.) THF, reflux, 2.) THF, RT, 10 h

2: 32 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 12 h / Ambient temperature

3: 75 percent / H₂ / 10percent Pd on C / methanol / 3.5 h / 760 Torr

4: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 - 20 deg C

5: 1.) Mg / 1.) Et₂O, 2.) Et₂O, -78 deg C, 2 h

6: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 - 20 deg C

7: 60 percent / NaBH₄ / ethanol / 1 h / 0 °C

8: hydrazine hydrate / ethanol / 2.5 h / Heating

9: Na₂CO₃ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With sodium tetrahydroborate; oxalyl dichloride; hydrogen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;
DOI:10.1021/jo00386a012

Reference yield:

: 99878-65-6
(1R,2S,3S)-4-(benzyloxy)-2,3-bis<(methoxymethyl)oxy>-1-(p-methoxyphenyl)-1-(1,3-dioxo-2-azindan-2-yl)butane

: 108394-49-6
(2S,3S,4S,5R)-5-<<(benzyloxy)carbonyl>amino>-3,4-bis<(methoxymethyl)oxy>-5-(p-methoxyphenyl)-2-pentanol

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / H₂ / 10percent Pd on C / methanol / 3.5 h / 760 Torr

2: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 - 20 deg C

3: 1.) Mg / 1.) Et₂O, 2.) Et₂O, -78 deg C, 2 h

4: 1.) oxalyl chloride, Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) -78 - 20 deg C

5: 60 percent / NaBH₄ / ethanol / 1 h / 0 °C

6: hydrazine hydrate / ethanol / 2.5 h / Heating

7: Na₂CO₃ / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With sodium tetrahydroborate; oxalyl dichloride; hydrogen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water;
DOI:10.1021/jo00386a012