(R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 173465-71-9
• Molecular Formula: C₆₇H₉₂NO₁₃P
• Molecular Weight: 1150.44

Synonyms:

Chemical Property of (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-4-yl ester

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Technology Process of (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-4-yl ester

There total 3 articles about (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-4-yl ester 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:

allyl 4,6-O-benzylidene-2-deoxy-2-(Fmoc-amino)-α-D-glucopyranoside → (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-4-yl ester (173465-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / DCC, DMAP

2: 91 percent / NaBH₃CN, HCl

3: 2.) mCPBA / 1.) tetrazole

With hydrogenchloride; dmap; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide;

DOI:10.1016/0040-4039(95)01863-D

Reference yield:

(R)-3-Tetradecanoyloxy-tetradecanoic acid (4aR,6S,7R,8R,8aS)-6-allyloxy-7-(9H-fluoren-9-ylmethoxycarbonylamino)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester → (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-4-yl ester (173465-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / NaBH₃CN, HCl

2: 2.) mCPBA / 1.) tetrazole

With hydrogenchloride; sodium cyanoborohydride; 3-chloro-benzenecarboperoxoic acid;

DOI:10.1016/0040-4039(95)01863-D

Reference yield:

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) + (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-tetrahydro-pyran-4-yl ester (173465-70-8) → (R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-4-yl ester (173465-71-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; Yield given. Multistep reaction; 1.) tetrazole;

DOI:10.1016/0040-4039(95)01863-D

upstream raw materials:

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine

(R)-3-Tetradecanoyloxy-tetradecanoic acid (2S,3R,4R,5S,6R)-2-allyloxy-6-benzyloxymethyl-3-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-tetrahydro-pyran-4-yl ester

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