2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran

Base Information

• Chemical Name: 2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran
• CAS No.: 197916-07-7
• Molecular Formula: C₃₀H₃₄O₅
• Molecular Weight: 474.597
• Mol file: 197916-07-7.mol

Synonyms:2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran

Chemical Property of 2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran

There total 3 articles about 2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran 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: 92.0%

allyl α-L-rhamnopyranoside (64650-81-3) + benzyl bromide (100-39-0) → 2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran (197916-07-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo971413u

Reference yield:

L-rhamnose (73-34-7) → 2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran (197916-07-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 1 h / 100 °C

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / -30 - 20 °C

With sulfuric acid; sodium hydride; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.orglett.0c03670

Reference yield:

L-rhamnose (6014-42-2) → 2-allyloxy-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran (197916-07-7)

Guidance literature:

Multi-step reaction with 2 steps

1: amberlite IR / 4 h / 90 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1039/d1cc03589d

upstream raw materials:

allyl α-L-rhamnopyranoside

benzyl bromide

L-rhamnose

L-rhamnose

Downstream raw materials:

(2S,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl 2,2,2-trichloroacetimidate

2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside

(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranose

allyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-acetyl-α-L-rhamnopyranoside

Refernces

• 1、 Lowary, Todd L.,Wang, Lei. "Synthesis of Rhamnolipid Derivatives Containing Ester Isosteres". supporting information. p. 9633 - 9637. Retrieved 2020/12/21.
• 2、 Larson, Daniel P.,Heathcock, Clayton H.. "Total synthesis of tricolorin A". . p. 8406 - 8418. Retrieved 2007/10/03.