(3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer

Base Information

• Chemical Name: (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer
• CAS No.: 1417721-81-3
• Molecular Formula: C₂₆H₃₄O₄
• Molecular Weight: 410.554
• Mol file: 1417721-81-3.mol

Synonyms:(3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer

Chemical Property of (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer

There total 5 articles about (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer 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: 43.0%

(2R)-hex-5-en-2-ol (17397-29-4) + C22H24Cl3NO4 (1417721-64-2) → (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer (1417721-81-3) + (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran β-anomer (1417721-82-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 - 0 ℃; for 3h;

DOI:10.1002/anie.201206797

Reference yield:

methyl 3,6-dideoxy-α-D-ribo-hexapyranoside (31899-66-8) → (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer (1417721-81-3) + (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran β-anomer (1417721-82-4)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

2: acetic acid; sulfuric acid / 2 h / 100 °C

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h

4: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -20 - 0 °C

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/anie.201206797

Reference yield:

(2S,3R,5S,6R)-3,5-bis(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran (85451-36-1) → (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer (1417721-81-3) + (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran β-anomer (1417721-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid; sulfuric acid / 2 h / 100 °C

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -20 - 0 °C

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1002/anie.201206797

upstream raw materials:

methyl 3,6-dideoxy-α-D-ribo-hexapyranoside

(2S,3R,5S,6R)-3,5-bis(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

(2R)-hex-5-en-2-ol

C₂₂H₂₄Cl₃NO₄

Downstream raw materials:

C₂₅H₃₂O₆