(2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene

Base Information

• Chemical Name: (2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene
• CAS No.: 187590-77-8
• Molecular Formula: C26H28O3S
• Molecular Weight: 420.573
• DSSTox Substance ID: DTXSID10442932
• Nikkaji Number: J1.511.111I
• Wikidata: Q82260545
• Mol file: 187590-77-8.mol

Synonyms:187590-77-8;(2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene;2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-epithio-D-arabinitol;(2R,3S,4S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)thiolane;C26H28O3S;SCHEMBL1856216;DTXSID10442932;IISDOLHHPNAZII-CYXNTTPDSA-N;MFCD23704946;AKOS016012240;DS-6717;A847921;2-O,3-O,5-O-Tribenzyl-1,4-dideoxy-1,4-epithio-D-arabinitol

Chemical Property of (2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene

Chemical Property:

• PSA: 52.99000
• LogP: 5.48940
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 420.17591592
• Heavy Atom Count: 30
• Complexity: 455

Purity/Quality:

95-99% ^*data from raw suppliers

(2R,?3S,?4S)?-?3,?4-?bis(benzyloxy)?-?2-?((benzyloxy)?methyl)?tetrahydrothiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(S1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: C1[C@H]([C@@H]([C@H](S1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Uses: (2R,?3S,?4S)?-?3,?4-?bis(benzyloxy)?-?2-?((benzyloxy)?methyl)?tetrahydrothiophene is an intermediate in the synthesis of Salacinol (S085200), salacinol is a α-glucosidase inhibitor discovered from the herb, Salacia reticulata. Salacinol is used as an antidiabetic agent.

Technology Process of (2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene

There total 8 articles about (2R,3S,4S)-3,4-Bis(benzyloxy)-2-((benzyloxy)methyl)tetrahydrothiophene 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: 90.0%

benzyl bromide (100-39-0) + 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose (160882-25-7) → 1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol (187590-77-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/jo001444g

Reference yield:

benzyl bromide (100-39-0) + (2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol (160882-26-8) → 1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol (187590-77-8)

Guidance literature:

(2R,3S,4S)-2-(hydroxymethyl)tetrahydrothiophene-3,4-diol; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 5 ℃; for 1h;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 3h;

Reference yield:

(2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane (135910-18-8) → 1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol (187590-77-8)

Guidance literature:

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

upstream raw materials:

benzyl chloride

3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose

benzyl bromide

(2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane

Downstream raw materials:

2,3,5-tri-O-benzyl-1,4-[(R)-[1-O-benzyl-4-deoxy-2-O-methyl-D-erythritol-4-yl]episulfoniumylidene]-1,4-dideoxy-D-arabitol chloride

Refernces

• 1、 -. "Compound useful for producing [...] and their production, production of [...], diol protecting group of deprotection method and method, as well as diol protecting groups (by machine translation)". Paragraph 0145. . Retrieved 2019/01/06.
• 2、 -. "COMPOUND USEFUL FOR MANUFACTURING SALACINOL, METHOD FOR MANUFACTURING THE COMPOUND, METHOD FOR MANUFACTURING SALACINOL, METHODS FOR PROTECTING AND DEPROTECTING DIOL GROUP, AND PROTECTIVE AGENT FOR DIOL GROUP". Paragraph 0422-0424. . Retrieved 2017/01/23.