64978-30-9

Basic information

• Product Name: .beta.-D-Glucopyranoside, 2-propenyl 1-thio-, tetraacetate
• Synonyms: .beta.-D-Glucopyranoside, 2-propenyl 1-thio-, tetraacetate
• CAS NO: 64978-30-9
• Molecular Formula: C17H24 O9 S
• Molecular Weight: 404.43
• Mol File: 64978-30-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .beta.-D-Glucopyranoside, 2-propenyl 1-thio-, tetraacetate(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Glucopyranoside, 2-propenyl 1-thio-, tetraacetate(64978-30-9)
• EPA Substance Registry System: .beta.-D-Glucopyranoside, 2-propenyl 1-thio-, tetraacetate(64978-30-9)

Safety Data

• Hazardous Substances Data: 64978-30-9(Hazardous Substances Data)

Upstream product

• 19879-84-6 O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose 
• 106-95-6 allyl bromide 
• 19879-84-6 tetraacetyl thioglucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 1076203-60-5 C₁₇H₂₄O₉SSe 
• 4671-92-5 allyl selenocyanate 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 72541-16-3 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose 
• 604-69-3 β-D-glucose pentaacetate 

Relevant articles and documents

Photooxidation of thiosaccharides mediated by sensitizers in aerobic and environmentally friendly conditions

A series of β-d-glucopyranosyl derivates have been synthesized and evaluated in photooxidation reactions promoted by visible light and mediated by organic dyes under aerobic conditions. Among the different photocatalysts employed, tetra-O-acetyl riboflavin afforded chemoselectively the respective sulfoxides, without over-oxidation to sulfones, in good to excellent yields and short reaction times. This new methodology for the preparation of synthetically useful glycosyl sulfoxides constitutes a catalytic, efficient, economical, and environmentally friendly oxidation process not reported so far for carbohydrates.

Stereoselective synthesis of β-glycosyl thiols and their synthetic applications

A significantly fast reaction condition for the exclusive preparation β-glycosyl thiol derivatives has been developed successfully. The reaction condition is one-step, fast, high yielding, highly stereoselective, and requires only benchtop chemicals. Further reaction of glycosyl thiol derivatives with Michael acceptors and alkylating agents furnished thioglycosides and (1,1)-thiolinked trehalose analogs.

Dechalcogenative allylic selenosulfide and disulfide rearrangements: Complementary methods for the formation of allylic sulfides in the absence of electrophiles. Scope, limitations, and application to the functionalization of unprotected peptides in aqueous media

Primary allylic selenosulfates (seleno Bunte salts) and selenocyanates transfer the allylic selenide moiety to thiols giving primary allylic selenosulfides, which undergo rearrangement in the presence of PPh3 with the loss of selenium to give allylically rearranged allyl alkyl sulfides. This rearrangement may be conducted with prenyl-type selenosulfides to give isoprenyl alkyl sulfides. Alkyl secondary and tertiary allylic disulfides, formed by sulfide transfer from allylic heteroaryl disulfides to thiols, undergo desulfurative allylic rearrangement on treatment with PPh3 in methanolic acetonitrile at room temperature. With nerolidyl alkyl disulfides this rearrangement provides an electrophile-free method for the introduction of the farnesyl chain onto thiols. Both rearrangements are compatible with the full range of functionality found in the proteinogenic amino acids, and it is demonstrated that the desulfurative rearrangement functions in aqueous media, enabling the derivatization of unprotected peptides. It is also demonstrated that the allylic disulfide rearrangement can be induced in the absence of phosphine at room temperature by treatment with piperidine, or simply by refluxing in methanol. Under these latter conditions the reaction is also applicable to allyl aryl disulfides, providing allylically rearranged allyl aryl sulfides in good yields.