(2R,3S,5S)-2-(((tert-Butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3-ol

Base Information

• Chemical Name: (2R,3S,5S)-2-(((tert-Butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3-ol
• CAS No.: 130144-85-3
• Molecular Formula: C₂₂H₃₀O₄Si
• Molecular Weight: 386.563
• DSSTox Substance ID: DTXSID20550719
• Wikidata: Q72490953
• Mol file: 130144-85-3.mol

Synonyms:(2R,3S,5S)-2-(((tert-Butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3-ol;130144-86-4;(2R,3S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methoxyoxolan-3-ol;(2R,3S,5S)-2-(((tert-Butyldiphenylsilyl)oxy)-methyl)-5-methoxytetrahydrofuran-3-ol;SCHEMBL8936662;DTXSID20550719;Methyl 5-O-[tert-butyl(diphenyl)silyl]-2-deoxy-alpha-D-erythro-pentofuranoside

Chemical Property of (2R,3S,5S)-2-(((tert-Butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3-ol

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 386.19133597
• Heavy Atom Count: 27
• Complexity: 434

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OCC3C(CC(O3)OC)O
• Isomeric SMILES: CC(C)(C)[Si](C1=CC=CC=C1)(C2=CC=CC=C2)OC[C@@H]3[C@H](C[C@H](O3)OC)O

Technology Process of (2R,3S,5S)-2-(((tert-Butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3-ol

There total 4 articles about (2R,3S,5S)-2-(((tert-Butyldiphenylsilyl)oxy)methyl)-5-methoxytetrahydrofuran-3-ol 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: 42.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → (2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran (130144-85-3) + (2R,3S,5R)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5β-methoxytetrahydrofuran (130144-86-4)

Guidance literature:

With pyridine hydrogenfluoride; at 20 ℃; for 20h;

DOI:10.1002/chem.200701567

Reference yield: 42.0%

methanol (67-56-1) + 2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran (130144-85-3) + (2R,3S,5R)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5β-methoxytetrahydrofuran (130144-86-4)

Guidance literature:

methanol; 2-deoxy-D-ribose; With hydrogenchloride; In diethyl ether; at 20 ℃; for 0.5h;

tert-butylchlorodiphenylsilane; With pyridine; at 20 ℃; for 18h;

DOI:10.1016/S0040-4020(02)00049-2

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → (2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5α-methoxytetrahydrofuran (130144-85-3) + (2R,3S,5R)-2-tert-butyldiphenylsilanyloxymethyl-3-hydroxy-5β-methoxytetrahydrofuran (130144-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / water monomer / 1 h / 24 °C

2: pyridine / 20 h / 24 °C / Inert atmosphere

With pyridine; hydrogenchloride; In water monomer;

DOI:10.1021/acs.chemrestox.1c00408

upstream raw materials:

methanol

D-2-deoxyribose

tert-butylchlorodiphenylsilane

1-O-methyl-2-deoxy-D-ribofuranoside

Downstream raw materials:

methyl 3-azido-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-α-D-erythro-pentofuranoside

(2R,3S,5S)-2-tert-butyldiphenylsilanyloxymethyl-3-benzyloxy-5α-methoxytetrahydrofuran

1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl)-N⁴-isobutyrylcytosine

1-(5-O-tert-butyldiphenylsilyl-3-(2-methoxycarbonylethyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl)-N⁴-isobutyrylcytosine