(2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran
• CAS No.: 294178-43-1
• Molecular Formula: C₁₄H₁₉N₃O₃
• Molecular Weight: 277.323
• Mol file: 294178-43-1.mol

Synonyms:(2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran

Chemical Property of (2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran

There total 19 articles about (2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran 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: 81.0%

(2S,3R,4R,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol (294178-42-0) → (2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran (294178-43-1)

Guidance literature:

With diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1002/1521-3773(20000616)39:12<2160::AID-ANIE2160>3.0.CO;2-E

Reference yield:

(2S,3R,4S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol (451505-76-3) → (2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran (294178-43-1)

Guidance literature:

Multi-step reaction with 3 steps

1: (COCl)2; DMSO; DIPEA / CH₂Cl₂

2: NaBH₄ / methanol

3: 81 percent / Ph₃P; (PhO)2P(O)N₃; DEAD / tetrahydrofuran

With sodium tetrahydroborate; oxalyl dichloride; diphenyl phosphoryl azide; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 1: Swern oxidation;

DOI:10.1016/S0960-894X(02)00209-3

Reference yield:

(2S,3S,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-one (72212-12-5) → (2S,3R,4S,6R)-4-Azido-3-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran (294178-43-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / methanol

2: 81 percent / Ph₃P; (PhO)2P(O)N₃; DEAD / tetrahydrofuran

With sodium tetrahydroborate; diphenyl phosphoryl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol;

DOI:10.1016/S0960-894X(02)00209-3

upstream raw materials:

(2S,3R,4R,6R)-3-Benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol

methyl 4,6-dideoxy-α-D-glucopyranoside

(2S,3R,4R,5S,6R)-5-chloro-6-(chloromethyl)-2-methoxytetrahydro-2H-pyran-3,4-diol

methyl-alpha-D-glucopyranoside

Downstream raw materials:

Phosphoric acid (2R,3R,4S,6R)-4-azido-3-benzyloxy-6-methyl-tetrahydro-pyran-2-yl ester dibenzyl ester