(2S,3R)-2-Azido-6-benzyloxy-3-tert-butoxycarbonylamino-hexanoic acid ethyl ester

Base Information

Chemical Name:(2S,3R)-2-Azido-6-benzyloxy-3-tert-butoxycarbonylamino-hexanoic acid ethyl ester
CAS No.:359015-21-7
Molecular Formula:C₂₀H₃₀N₄O₅
Molecular Weight:406.482
Hs Code.:

Synonyms:(2S,3R)-2-Azido-6-benzyloxy-3-tert-butoxycarbonylamino-hexanoic acid ethyl ester

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Chemical Property of (2S,3R)-2-Azido-6-benzyloxy-3-tert-butoxycarbonylamino-hexanoic acid ethyl ester

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Technology Process of (2S,3R)-2-Azido-6-benzyloxy-3-tert-butoxycarbonylamino-hexanoic acid ethyl ester

There total 6 articles about (2S,3R)-2-Azido-6-benzyloxy-3-tert-butoxycarbonylamino-hexanoic acid ethyl ester 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%

: 359015-31-9
(2R,3R)-6-Benzyloxy-3-tert-butoxycarbonylamino-2-hydroxy-hexanoic acid ethyl ester

: 359015-21-7
(2S,3R)-2-Azido-6-benzyloxy-3-tert-butoxycarbonylamino-hexanoic acid ethyl ester

Guidance literature:: With tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; benzene;
DOI:10.1016/S0040-4039(01)00757-2

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 359015-21-7
(2S,3R)-2-Azido-6-benzyloxy-3-tert-butoxycarbonylamino-hexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / DBU; LiCl / acetonitrile / 0 °C

2: 65 percent / NaOH; tBuOCl; (DHQD)2PHAL / K₂[OsO₂(OH)4] / propan-1-ol; H₂O / 1 h / 0 °C

3: 84 percent / DEAD; Ph₃P / tetrahydrofuran

4: 95 percent / K₂CO₃ / methanol

5: 80 percent / HN₃; DEAD; Ph₃P / benzene; tetrahydrofuran

With sodium hydroxide; tert-butylhypochlorite; tris-(2-chloro-ethyl)-amine; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; lithium chloride; diethylazodicarboxylate; K2; In tetrahydrofuran; methanol; propan-1-ol; water; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)00757-2

Reference yield:

: 4541-14-4
4-benzyloxy-butan-1-ol

: 359015-21-7
(2S,3R)-2-Azido-6-benzyloxy-3-tert-butoxycarbonylamino-hexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2: 82 percent / DBU; LiCl / acetonitrile / 0 °C

3: 65 percent / NaOH; tBuOCl; (DHQD)2PHAL / K₂[OsO₂(OH)4] / propan-1-ol; H₂O / 1 h / 0 °C

4: 84 percent / DEAD; Ph₃P / tetrahydrofuran

5: 95 percent / K₂CO₃ / methanol

6: 80 percent / HN₃; DEAD; Ph₃P / benzene; tetrahydrofuran

With sodium hydroxide; oxalyl dichloride; tert-butylhypochlorite; tris-(2-chloro-ethyl)-amine; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; lithium chloride; diethylazodicarboxylate; K2; In tetrahydrofuran; methanol; propan-1-ol; dichloromethane; water; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)00757-2