105938-03-2

Basic information

• Product Name: (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol
• Synonyms: (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol
• CAS NO: 105938-03-2
• Molecular Weight: 448.559
• Mol File: 105938-03-2.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol(105938-03-2)
• EPA Substance Registry System: (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol(105938-03-2)

Safety Data

• Hazardous Substances Data: 105938-03-2(Hazardous Substances Data)

Upstream product

• 74-88-4 methyl iodide 
• 100-39-0 benzyl bromide 
• 13265-84-4 D-glucal 
• 79999-47-6 tri-O-(tert-butyldimethylsilyl)-D-glucal 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 1011723-04-8 glucal epoxide 
• 917-54-4 methyllithium 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 77-78-1 dimethyl sulfate 
• 161145-52-4 triphenyl(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)stannane 
• 105938-02-1 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol 

Downstream Products

• 105938-04-3 Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI50 values) below 10 μM, the C-gluco

C-Glycosides to fused polycyclic ethers

This manuscript describes the synthesis of fused polycyclic ethers from the coupling of C-glycoside forming reactions with ring closing metathesis and acid mediated annulation reactions.

Preparation and transmetallation of a triphenylstannyl β-D-glucopyranoside: A highly stereoselective route to β-D-C-glycosides via glycosyl dianions

The triphenylstannyl β-D-glucopyranoside 4 was synthesized in one step from the 1,2-anhydro-α-D-glucopyranose 3 with (triphenylstannyl)lithium. Transmetallation of 4 with excess BuLi, followed by quenching the dianion 7 with CD3OD gave (IS)-1,5-anhydro-3,4,6-tri-o-benzyl-[1-2H]-D-glucitol (8) in 81% yield. Trapping of 7 with benzaldehyde, isobutyraldehyde, or acroleine gave the expected β-D-configurated products 11, 12, and 13 in good yields. Preparation of C-acyl glycosides from acid chlorides, such as acetyl or benzoyl chloride was not practicable, but addition of benzonitrile to 7 yielded 84% of the benzoylated product 14. Treatment of 7 with MeI led to 15 (30%) along with 40% of 18, C-alkylation being accompanied by halogen-metal exchange. Prior addition of lithium 2-thienylcyanocuprate increased the yield of 15 to 50% and using dimethyl sulfate instead of MeI led to 77% of 15. No α-D-anomers could be detected, except with allyl bromide as the electrophile, which yielded in a 1:1 mixture of the anomers 16 and 17.

Formation of C-Glycosides by Polarity Inversion at the Anomeric Centre

Alkylation of 1-lithio trisubstituted glycals obtained via the corresponding 1-tributylstannyl derivatives constitutes a novel entry into C-glycosides.