5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

Base Information

Chemical Name:5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol
CAS No.:264872-39-1
Molecular Formula:C₂₆H₃₇NO₅
Molecular Weight:443.583
Hs Code.:

Synonyms:5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

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Chemical Property of 5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

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Technology Process of 5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

There total 10 articles about 5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol 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: 91.0%

: 264872-38-0
5-O-benzyl-2-[(tert-butoxycarbonyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

: 74-88-4
methyl iodide

: 264872-39-1
5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1016/S0040-4020(99)01052-2

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 264872-39-1
5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / Et₃N; DMAP / tetrahydrofuran / 2 h / 23 °C

2: 91 percent / NaH / dimethylformamide / 18 h / 20 °C

With dmap; sodium hydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Acylation / 2: Methylation;
DOI:10.1016/S0040-4020(99)01052-2

Reference yield:

: 89923-31-9
(E)-5-(benzyloxy)pent-2-en-1-ol

: 264872-39-1
5-O-benzyl-2-[(tert-butoxycarbonyl)(methyl)amino]-1,2,4-trideoxy-3-O-(methoxymethyl)-1-phenyl-D-threo-pentitol

Guidance literature:: Multi-step reaction with 9 steps

1: 94 percent / NCS; DMs / CH₂Cl₂ / 0 - 20 °C

2: 95 percent / (DHQD)2PHAL; K₂OsO₂(OH)4; K₃[F₃(CN)6] / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

3: 89 percent / NaOH / tetrahydrofuran / 2 h / 0 °C

4: 89 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

5: 94 percent / CuCn / tetrahydrofuran; diethyl ether; cyclohexane / 8 h / -20 °C

6: 8 percent / PPh₃; DEADF; diphenylphosphoryl azide / tetrahydrofuran / 0 - 23 °C

7: 86 percent / LiAlH₄ / diethyl ether / 3 h / 20 °C

8: 92 percent / Et₃N; DMAP / tetrahydrofuran / 2 h / 23 °C

9: 91 percent / NaH / dimethylformamide / 18 h / 20 °C

With dmap; sodium hydroxide; N-chloro-succinimide; lithium aluminium tetrahydride; potassium dioxotetrahydroxoosmate(VI); 2,3-dimercapto-succinic acid; diphenylphosphoranyl azide; sodium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; potassium hexacyanoferrate(III); In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Substitution / 2: Sharpless asymmetric dihydroxylation / 3: Cyclization / 4: Etherification / 5: Ring cleavage / 6: Substitution / 7: Reduction / 8: Acylation / 9: Methylation;
DOI:10.1016/S0040-4020(99)01052-2