(1R,2R,3R,5S)-3-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol

Base Information

• Chemical Name: (1R,2R,3R,5S)-3-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol
• CAS No.: 76910-01-5
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.144
• Mol file: 76910-01-5.mol

Synonyms:(1R,2R,3R,5S)-3-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol

Chemical Property of (1R,2R,3R,5S)-3-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,5S)-3-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol

There total 1 articles about (1R,2R,3R,5S)-3-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-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:

4-(hydroxymethyl)cyclopentene (25125-21-7) → 1β-Hydroxymethyl-2α-hydroxy-3α,4α-epoxycyclopentane (76910-01-5,122798-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / SeO₂ / tetrahydrofuran; 1,2-dimethoxy-ethane / 18 h / 64 °C

2: m-chloroperbenzoic acid / CH₂Cl₂ / 1.33 h / Ambient temperature

With selenium(IV) oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1002/jhet.5570260235

Reference yield: 74.0%

benzyl bromide (100-39-0) + (1R,2R,3R,5S)-3-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol (76910-01-5) → (1S,2R,3R,5S)-2-Benzyloxy-3-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane (324742-00-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)01704-4

Reference yield:

(1R,2R,3R,5S)-3-(hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol (76910-01-5) → 1-((1R,2S,3R,4R)-3-Benzyloxy-4-benzyloxymethyl-2-hydroxy-cyclopentyl)-1H-[1,2,4]triazole-3-carboxylic acid amide

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / NaH / tetrahydrofuran

2: 40 percent / NaH / dimethylformamide / 110 °C

3: 100 percent / NH₃ / methanol

With ammonia; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)01704-4

upstream raw materials:

4-(hydroxymethyl)cyclopentene

Downstream raw materials:

(+/-)-(1α,2α,3β,5β)-3-amino-5-(hydroxymethyl)-1,2-cyclopentanediol

(1S,2R,3R,5S)-2-Benzyloxy-3-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane

1-((1R,2S,3R,4R)-3-Benzyloxy-4-benzyloxymethyl-2-hydroxy-cyclopentyl)-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester