((4S,5R,6S)-4-Azido-5,6-bis-benzyloxy-7-hydroxy-heptyl)-benzyl-carbamic acid tert-butyl ester

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Chemical Name:((4S,5R,6S)-4-Azido-5,6-bis-benzyloxy-7-hydroxy-heptyl)-benzyl-carbamic acid tert-butyl ester
CAS No.:602298-25-9
Molecular Formula:C₃₃H₄₂N₄O₅
Molecular Weight:574.72
Hs Code.:

Synonyms:((4S,5R,6S)-4-Azido-5,6-bis-benzyloxy-7-hydroxy-heptyl)-benzyl-carbamic acid tert-butyl ester

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Chemical Property of ((4S,5R,6S)-4-Azido-5,6-bis-benzyloxy-7-hydroxy-heptyl)-benzyl-carbamic acid tert-butyl ester

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Technology Process of ((4S,5R,6S)-4-Azido-5,6-bis-benzyloxy-7-hydroxy-heptyl)-benzyl-carbamic acid tert-butyl ester

There total 11 articles about ((4S,5R,6S)-4-Azido-5,6-bis-benzyloxy-7-hydroxy-heptyl)-benzyl-carbamic acid tert-butyl 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: 79.0%

: 100-39-0
benzyl bromide

: 602298-24-8
carbonic acid 4-azido-2,3-bis-benzyloxy-7-tert-butoxycarbonylamino-heptyl ester tert-butyl ester

: 602298-25-9
((4S,5R,6S)-4-Azido-5,6-bis-benzyloxy-7-hydroxy-heptyl)-benzyl-carbamic acid tert-butyl ester

Guidance literature:: With sodium hydride; In dichloromethane; at 0 - 20 ℃; for 6h;
DOI:10.1016/S0040-4039(03)01368-6

Reference yield:

: 4099-85-8,5531-21-5,20672-63-3,20672-65-5,58763-00-1,63029-07-2,72402-14-3,84894-45-1,129263-68-9,828937-29-7
methyl 2,3-O-isopropylidene-D-ribofuranoside

: 602298-25-9
((4S,5R,6S)-4-Azido-5,6-bis-benzyloxy-7-hydroxy-heptyl)-benzyl-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: (COCl)2; Et₃N / dimethylsulfoxide / -78 - 20 °C

1.2: 79 percent / CH₂Cl₂ / 1 h / 20 °C

2.1: 87 percent / LAH / tetrahydrofuran / 6 h / 0 - 20 °C

3.1: TsCl; Et₃N / CH₂Cl₂ / 6 h / 0 - 20 °C

3.2: 74 percent / NaN₃ / dimethylformamide / 8 h / 90 °C

4.1: 86 percent / MeOH; HCl / 4 h / 60 °C

5.1: 92 percent / NaH / dimethylformamide / 2 h / 0 - 20 °C

6.1: 76 percent / AcOH; water; HCl / 2 h / 60 °C

7.1: LAH / tetrahydrofuran / 0.5 h / 0 °C

7.2: 93 percent / NaOH; water / 12 h

8.1: MsCl; Et₃N / CH₂Cl₂ / 6 h / 0 - 20 °C

8.2: 93 percent / NaN₃ / CH₂Cl₂ / 12 h / 90 °C

9.1: 79 percent / NaH / CH₂Cl₂ / 6 h / 0 - 20 °C

With hydrogenchloride; methanol; lithium aluminium tetrahydride; oxalyl dichloride; water; sodium hydride; acetic acid; methanesulfonyl chloride; triethylamine; p-toluenesulfonyl chloride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(03)01368-6

Reference yield:

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

: 602298-25-9
((4S,5R,6S)-4-Azido-5,6-bis-benzyloxy-7-hydroxy-heptyl)-benzyl-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: LAH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 93 percent / NaOH; water / 12 h

2.1: MsCl; Et₃N / CH₂Cl₂ / 6 h / 0 - 20 °C

2.2: 93 percent / NaN₃ / CH₂Cl₂ / 12 h / 90 °C

3.1: 79 percent / NaH / CH₂Cl₂ / 6 h / 0 - 20 °C

With lithium aluminium tetrahydride; sodium hydride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(03)01368-6