1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol

Base Information

• Chemical Name: 1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol
• CAS No.: 153165-85-6
• Molecular Formula: C₂₀H₂₃NO₃
• Molecular Weight: 325.408
• Mol file: 153165-85-6.mol

Synonyms:1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol

Chemical Property of 1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol

There total 5 articles about 1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol 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: 95.0%

1R-(1β,4α,5β,6β) 4-azido-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol (153165-83-4) → 1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol (153165-85-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 0.75h; Heating;

DOI:10.1016/S0040-4020(01)87223-9

Reference yield:

benzyl bromide (100-39-0) → 1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol (153165-85-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / dimethylformamide / 0 °C

2: 75 percent / Hg(CF₃CO₂)2 / acetone; H₂O / 20 °C

3: 72 percent / mesyl chloride, pyridine / CH₂Cl₂ / 10 h / Ambient temperature

4: 78 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.75 h

5: 95 percent / LiAlH₄ / diethyl ether / 0.75 h / Heating

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; Hg(II) trifluoroacetate; sodium hydride; methanesulfonyl chloride; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)87223-9

Reference yield:

4R-(4α,5β,6β) 4-azido-5,6-bis(phenylmethoxy)-2-cyclohexen-1-one (95308-53-5) → 1R-(1β,4α,5β,6β) 4-amino-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol (153165-85-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.75 h

2: 95 percent / LiAlH₄ / diethyl ether / 0.75 h / Heating

With sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride; In methanol; diethyl ether;

DOI:10.1016/S0040-4020(01)87223-9

upstream raw materials:

1R-(1β,4α,5β,6β) 4-azido-5,6-bis(phenylmethoxy)-2-cyclohexen-1-ol

benzyl bromide

4R-(4α,5β,6β) 4-azido-5,6-bis(phenylmethoxy)-2-cyclohexen-1-one

2S-(2β,3β,4α,5α) 4-azido-5-hydroxy-2,3-bis(phenylmethoxy)-cyclohexanone

Downstream raw materials:

<1R-(1α,4β,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-2,3,4-tris-(methoxy)-benzamide

<1R-(1α,4β,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-benzamide

<1R-(1α,4β,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-1,3 benzodioxole-4-hydroxy-5-carboxamide

<1R-(1α,4β,5β,6β)> N-<5,6-bis(phenylmethoxy)-4-hydroxy-2-cyclohexen-1-yl>-3,4-bis-(methoxy)-benzamide

Refernces