Methyl 2,3-o-isopropylidene-alpha-l-rhamnopyranoside

Base Information

• Chemical Name: Methyl 2,3-o-isopropylidene-alpha-l-rhamnopyranoside
• CAS No.: 14133-63-2
• Molecular Formula: C10H18 O5
• Molecular Weight: 218.25
• DSSTox Substance ID: DTXSID60447270
• Nikkaji Number: J184.533K
• Wikidata: Q63399712
• Mol file: 14133-63-2.mol

Synonyms:14133-63-2;methyl 2,3-o-isopropylidene-alpha-l-rhamnopyranoside;(3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-7-ol;(3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol;(3aR,4R,6S,7S,7aR)-4-Methoxy-2,2,6-trimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol;Methyl 2,3-O-isopropylidene-a-L-rhamnopyranoside;METHYL 2,3-O-ISOPROPYLIDENE-ALPHA-L-RHAMNOPYRANOSIDE (2,2,2,3,3,3-D6);SCHEMBL7152448;DTXSID60447270;CS-0254929;Methyl 3-amino-3-deoxy-a-D-mannopyranoside HCl;W-201214;Q63399712;Methyl 2-O,3-O-isopropylidene-alpha-L-rhamnopyranoside;Methyl 6-deoxy-2,3-O-(1-methylethylidene)-alpha-L-mannopyranoside;(3aR,4R,6S,7S,7aR)-4-methoxy-2,2,6-trimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

Chemical Property of Methyl 2,3-o-isopropylidene-alpha-l-rhamnopyranoside

Chemical Property:

• PSA: 57.15000
• LogP: 0.25860
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 218.11542367
• Heavy Atom Count: 15
• Complexity: 242

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 2,3-O-isopropylidene-a-L-rhamnopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C2C(C(O1)OC)OC(O2)(C)C)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@@H]2[C@H]([C@@H](O1)OC)OC(O2)(C)C)O

Technology Process of Methyl 2,3-o-isopropylidene-alpha-l-rhamnopyranoside

There total 39 articles about Methyl 2,3-o-isopropylidene-alpha-l-rhamnopyranoside 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: 100.0%

methyl 2,3-O-isopropylidene-6-O-p-toluenesulfonyl-α-D-mannopyranoside (112612-45-0) → methyl 2,3-O-isopropylidene-α-D-rhamnopyranoside (14133-63-2,14685-82-6,22932-38-3,24562-43-4,33947-10-3,42214-01-7,52572-07-3,72251-91-3,72251-92-4,72959-81-0,104846-19-7,149035-63-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 30 ℃; for 6h;

DOI:10.1016/0008-6215(88)80144-7

Reference yield: 99.0%

2,2-dimethoxy-propane (77-76-9) + methyl 6-deoxy-α-L-mannopyranoside (14917-55-6) → methyl 2,3-O-isopropylidene-α-L-rhamnoside (14133-63-2)

Guidance literature:

With toluene-4-sulfonic acid; for 2h;

Reference yield: 98.0%

methyl 6-deoxy-6-iodo-2,3-O-isopropylidene-α-D-mannopyranoside (22932-34-9) → methyl 2,3-O-isopropylidene-α-D-rhamnopyranoside (14133-63-2,14685-82-6,22932-38-3,24562-43-4,33947-10-3,42214-01-7,52572-07-3,72251-91-3,72251-92-4,72959-81-0,104846-19-7,149035-63-2)

Guidance literature:

With palladium on activated charcoal; hydrogen; triethylamine; In ethanol; at 21 ℃; for 16h;

DOI:10.1021/ja5081184

upstream raw materials:

methyl-[O²,O³-isopropylidene-O⁴-(toluene-4-sulfonyl)-α-L-rhamnopyranoside]

methanol

L-Rhamnose

acetone

Downstream raw materials:

methyl 4-O-benzoyl-2,3-O-isopropylidene-α-D-rhamnopyranoside

Refernces

• 1、 -. "USE OF FUCOSYLATION INHIBITOR FOR PRODUCING AFUCOSYLATED ANTIBODY". Page/Page column 5; 19-21. . Retrieved 2021/06/26.
• 2、 Wu, Jingjing,B?r, Robin M.,Guo, Lin,Noble, Adam,Aggarwal, Varinder K.. "Photoinduced Deoxygenative Borylations of Aliphatic Alcohols". supporting information. p. 18830 - 18834. Retrieved 2019/11/22.