(1S,2R,3S,5R)-3-(Benzyloxy)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexane

Base Information

• Chemical Name: (1S,2R,3S,5R)-3-(Benzyloxy)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexane
• CAS No.: 110567-22-1
• Molecular Formula: C20H22O3
• Molecular Weight: 310.393
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID40454442
• Nikkaji Number: J1.164.218G
• Wikidata: Q72497601
• Mol file: 110567-22-1.mol

Synonyms:110567-22-1;(1S,2R,3S,5R)-3-(Benzyloxy)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexane;(1S,2R,3S,5R)-3-(Phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane;(1S,2R,3S,5R)-3-phenylmethoxy-2-(phenylmethoxymethyl)-6-oxabicyclo[3.1.0]hexane;(1S,2R,3S,5R)-3-(Phenymethyloxy)-2-(phenylmethoxy)methyl-6-oxabicyclo[3.1.0]hexane;(1S,2R,3S,5R)-3-(Benzyloxy)-2-[(benzyloxy)methyl]-6-oxabicyclo[3.1.0]hexane;[1S-(1alpha,2alpha,3beta,5alpha)]-3-(Phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane;SCHEMBL2531282;DTXSID40454442;AMY40508;MFCD09750952;AKOS015918406;AC-5918;(1S,2R,3S,5R)-3-(Benzyloxy)-2-((benzyloxy)-methyl)-6-oxabicyclo[3.1.0]hexane;(1S,2R,3S,5R)-3-(benzyloxy)-2-[(benzyloxy)methyl]-6-oxa hexagon[3.1.0]hexane;6-Oxabicyclo[3,1,0]hexane-3-(phenylmetyoxy)-2-[(phenylmethoxy)methyl]-(1S,2R,3S,5R);AS-19494;CS-0132707;W-204743;(1alpha,5alpha)-2alpha-[(Benzyloxy)methyl]-3beta-(benzyloxy)-6-oxabicyclo[3.1.0]hexane;(1S,2R,3S,5R)-3-(benzyloxy)-2-(benzyloxymethyl)-6-oxabicyclo[3.1.0]hexane;(1S,2R,3S,5R)-3-(Phenylmethoxy)-2 -[(phenylmethoxy)methyl]-6- oxabicyclo[3.1.0]hexane;[1S-(1 alpha ,2 alpha ,3 beta ,5 alpha )]-3-(Phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane;[1S-(1?,2?,3?,5?)]-3-(Phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane

Chemical Property of (1S,2R,3S,5R)-3-(Benzyloxy)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexane

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.593
• Boiling Point: 427.928 °C at 760 mmHg
• Flash Point: 145.852 °C
• PSA: 30.99000
• Density: 1.174 g/cm³
• LogP: 3.57590
• Storage Temp.: Refrigerator
• Solubility.: Benzene, Chloroform, DMSO, Methanol
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 310.15689456
• Heavy Atom Count: 23
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

[1S-(1α,2α,3β,5α)]-3-(Phenylmethoxy)-2-[(phenylmethoxy)methyl]-6-oxabicyclo[3.1.0]hexane ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(O2)C(C1OCC3=CC=CC=C3)COCC4=CC=CC=C4
• Isomeric SMILES: C1[C@@H]2[C@@H](O2)[C@@H]([C@H]1OCC3=CC=CC=C3)COCC4=CC=CC=C4
• Uses: Entecavir intermediate. Entecavir intermediate

Technology Process of (1S,2R,3S,5R)-3-(Benzyloxy)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexane

There total 9 articles about (1S,2R,3S,5R)-3-(Benzyloxy)-2-((benzyloxy)methyl)-6-oxabicyclo[3.1.0]hexane 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: 95.85%

(3R,4S)-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopent-1-ene (191480-69-0) → (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane (110567-22-1)

Guidance literature:

With dihydrogen peroxide; 3C₂₇H₃₃N₂O₂⁽¹⁺⁾*PW₄O₂₄^(3-); In dichloromethane; at 20 ℃; Concentration;

Reference yield: 86.0%

benzyl bromide (100-39-0) + (2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol (117641-39-1) → (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane (110567-22-1)

Guidance literature:

(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 1h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1055/s-2003-41455

Reference yield:

(1S,2R)-2-(benzyloxymethyl)-1-hydroxy-3-cyclopentene (110567-21-0) → (2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane (110567-22-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 82 percent / Mo(CO)6; t-BuOOH / benzene; decane / 3 h / 80 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: 86 percent / tetrabutylammonium iodide / tetrahydrofuran / 12 h / 20 °C

With tert.-butylhydroperoxide; hexacarbonyl molybdenum; sodium hydride; In tetrahydrofuran; decane; benzene;

DOI:10.1055/s-2003-41455

upstream raw materials:

benzyl bromide

(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol

Benzyloxymethyl chloride

5-(benzyloxymethyl)cyclopentadiene

Downstream raw materials:

(1S,2S,3S,5S)-5-azido-3-(benzyloxy)-2-(benzyloxymethyl)cyclopentanol

1-((1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl)-5-methylpyrimidine-2,4(1H,3H)-dione

(1S,3S,4S)-3-(benzyloxy)-4-(benzyloxymethyl)cyclopentanol

(1R,3S,4S)-3-(benzyloxy)-4-(benzyloxymethyl)cyclopentanol

Refernces

• 1、 -. "Preparation method of oxa-dicyclohexane compound". Paragraph 0026-0028; 0032-0034; 0038-0046. . Retrieved 2021/06/26.
• 2、 Tran, Scott B.,Ekhato, Ihoezo V.,Rinehart, J. Kent. "Synthesis of [13C4]Baraclude (entecavir)". scheme or table. p. 485 - 489. Retrieved 2010/07/04.