4-Cyclohexene-1,2,3-triol, 6-amino-4-methyl-, (1R,2R,3R,6S)-rel- (9CI)

Base Information

• Chemical Name: 4-Cyclohexene-1,2,3-triol, 6-amino-4-methyl-, (1R,2R,3R,6S)-rel- (9CI)
• CAS No.: 432547-05-2
• Molecular Formula: C₇H₁₃NO₃
• Molecular Weight: 159.185
• Mol file: 432547-05-2.mol

Synonyms:4-Cyclohexene-1,2,3-triol, 6-amino-4-methyl-, (1R,2R,3R,6S)-rel- (9CI)

Chemical Property of 4-Cyclohexene-1,2,3-triol, 6-amino-4-methyl-, (1R,2R,3R,6S)-rel- (9CI)

Chemical Property:

• PSA: 0.00000
• LogP: 0.00000

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 4-Cyclohexene-1,2,3-triol, 6-amino-4-methyl-, (1R,2R,3R,6S)-rel- (9CI)

There total 16 articles about 4-Cyclohexene-1,2,3-triol, 6-amino-4-methyl-, (1R,2R,3R,6S)-rel- (9CI) 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:

(1S,4R,5R,6R)-4,5,6-Tris-methoxymethoxy-3-methyl-cyclohex-2-enylamine → (1R,2R,3R,6S)-6-Amino-4-methyl-cyclohex-4-ene-1,2,3-triol (432547-04-1,461025-36-5,432547-05-2)

Guidance literature:

With hydrogenchloride; at 60 ℃;

DOI:10.1016/S0960-894X(02)00004-5

Reference yield:

(1R,4R,5R,6R)-4,5,6-Tris-methoxymethoxy-3-methyl-cyclohex-2-enylamine → (1R,2R,3R,6R)-6-Amino-4-methyl-cyclohex-4-ene-1,2,3-triol (432547-04-1,461025-36-5,432547-05-2)

Guidance literature:

With hydrogenchloride; at 60 ℃;

DOI:10.1016/S0960-894X(02)00004-5

Reference yield:

(1RS,2SR,3RS)-1,2,3-tri-O-acetyl-6-methylene-4-cyclohexene-1,2,3-triol → (1R,2R,3R,6S)-6-Amino-4-methyl-cyclohex-4-ene-1,2,3-triol (432547-04-1,461025-36-5,432547-05-2)

Guidance literature:

Multi-step reaction with 7 steps

1: NaOMe / methanol / 20 °C

2: (iPr)2NEt / CH₂Cl₂ / 40 °C

3: Br₂ / CCl₄ / 20 °C

4: 57 percent / NaBH₄ / hexamethylphosphoric acid triamide / 20 °C

5: 88 percent / NaN₃ / dimethylformamide / 20 °C

6: 33 percent / PPh₃ / tetrahydrofuran; H₂O / 60 °C

7: 4 M HCl / 60 °C

With hydrogenchloride; sodium tetrahydroborate; sodium azide; bromine; sodium methylate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(02)00004-5

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