3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide

Base Information

• Chemical Name: 3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide
• CAS No.: 211231-33-3
• Molecular Formula: C₄₄H₄₇O₁₀P
• Molecular Weight: 766.825
• Mol file: 211231-33-3.mol

Synonyms:

Chemical Property of 3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide

There total 10 articles about 3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide 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:

3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine → 3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide (211231-33-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -60 ℃; for 0.25h; Yield given;

DOI:10.1016/S0008-6215(98)00037-8

Reference yield:

methyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside (23392-28-1) → 3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide (211231-33-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / NaH (50percent oil susp.) / dimethylformamide / 3 h

2: 96 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.75 h / Heating

3: (COCl)2, Me₂SO / CH₂Cl₂ / 1 h / -60 °C

4: 32 percent / Mg / tetrahydrofuran / 14 h

5: 87.6 percent / NaH (50percent oil susp.) / dimethylformamide / 8 h

6: 90.9 percent / 1,4-diaminobicyclo<2.2.2>octane / Wilkinson's catalyst / ethanol; benzene; H₂O / 3 h / Heating

7: tetrazole / CH₂Cl₂ / 2 h / Ambient temperature

8: m-ClC₆H₄CO₃H / CH₂Cl₂ / 0.25 h / -60 °C

With 1H-tetrazole; lithium aluminium tetrahydride; aluminium trichloride; oxalyl dichloride; bicyclo[2.2.2] octane-1,4-diamine; sodium hydride; magnesium; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0008-6215(98)00037-8

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide (211231-33-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 32 percent / Mg / tetrahydrofuran / 14 h

2: 87.6 percent / NaH (50percent oil susp.) / dimethylformamide / 8 h

3: 90.9 percent / 1,4-diaminobicyclo<2.2.2>octane / Wilkinson's catalyst / ethanol; benzene; H₂O / 3 h / Heating

4: tetrazole / CH₂Cl₂ / 2 h / Ambient temperature

5: m-ClC₆H₄CO₃H / CH₂Cl₂ / 0.25 h / -60 °C

With 1H-tetrazole; bicyclo[2.2.2] octane-1,4-diamine; sodium hydride; magnesium; 3-chloro-benzenecarboperoxoic acid; Wilkinson's catalyst; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0008-6215(98)00037-8

upstream raw materials:

Benzyloxymethyl chloride

methyl 3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

(1,5-Dihydro-benzo[e][1,3,2]dioxaphosphepin-3-yl)-dimethyl-amine

methyl 2-O-allyl-3-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside