(1R,2S,3S,4R,6S)-4,6-Diazido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

Base Information

Chemical Name:(1R,2S,3S,4R,6S)-4,6-Diazido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol
CAS No.:549501-30-6
Molecular Formula:C₂₆H₃₀N₁₂O₆
Molecular Weight:606.601
Hs Code.:

Synonyms:(1R,2S,3S,4R,6S)-4,6-Diazido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

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Chemical Property of (1R,2S,3S,4R,6S)-4,6-Diazido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

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Technology Process of (1R,2S,3S,4R,6S)-4,6-Diazido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

There total 7 articles about (1R,2S,3S,4R,6S)-4,6-Diazido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol 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: 37.0%

: 549501-24-8
(1S,2R,3R,4S,6R)-4,6-Diazido-3-methoxymethoxy-cyclohexane-1,2-diol

: 549501-23-7
(3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-phenylsulfanyl-tetrahydro-pyran

: 549501-29-3
(1R,2R,3S,4R,6S)-4,6-Diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,3-diol

: (1R,2R,3S,4R,6S)-4,6-Diazido-2-((2S,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,3-diol

: 549501-30-6
(1R,2S,3S,4R,6S)-4,6-Diazido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

: (1R,2S,3S,4R,6S)-4,6-Diazido-3-((2S,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

Guidance literature:: (1S,2R,3R,4S,6R)-4,6-Diazido-3-methoxymethoxy-cyclohexane-1,2-diol; (3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-phenylsulfanyl-tetrahydro-pyran; With N-iodo-succinimide; silver trifluoromethanesulfonate; In diethyl ether; dichloromethane; at -20 ℃;

With hydrogenchloride; In methanol; at 75 ℃;
DOI:10.1016/S0960-894X(02)01073-9

Reference yield:

: 549501-23-7
(3R,4R,5R,6R)-3-Azido-6-azidomethyl-4,5-bis-benzyloxy-2-phenylsulfanyl-tetrahydro-pyran

: 549501-30-6
(1R,2S,3S,4R,6S)-4,6-Diazido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: N-iodo-succinimide; silver trifluoromethanesulfonate / diethyl ether; dichloromethane / -15 °C

2: sodium methylate / methanol

With N-iodo-succinimide; sodium methylate; silver trifluoromethanesulfonate; In methanol; diethyl ether; dichloromethane;

Reference yield:

: 171032-74-9
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 549501-30-6
(1R,2S,3S,4R,6S)-4,6-Diazido-3-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 7 steps

1: zinc(II) iodide / 1,2-dichloro-ethane / 50 °C

2: sodium methylate / methanol

3: pyridine

4: sodium azide / DMF (N,N-dimethyl-formamide) / 80 °C

5: sodium hydride / DMF (N,N-dimethyl-formamide)

6: N-iodo-succinimide; silver trifluoromethanesulfonate / diethyl ether; dichloromethane / -15 °C

7: sodium methylate / methanol

With pyridine; N-iodo-succinimide; sodium azide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; zinc(II) iodide; In methanol; DMF (N,N-dimethyl-formamide); diethyl ether; dichloromethane; 1,2-dichloro-ethane;